68576-86-3Relevant articles and documents
New chemical and chemo-enzymatic routes for the synthesis of (RS)- and (S)-enciprazine
Banoth, Linga,Narayan, Thete Karuna,Banerjee, Uttam C.
, p. 1272 - 1278 (2012/11/07)
The chemo-enzymatic synthesis of racemic and enantiopure (RS)- and (S)-enciprazine 1, a non-benzodiazepine anxiolytic drug, is described herein. The synthesis started from 1-(2-methoxyphenyl) piperazine 3, which was treated with 2-(chloromethyl) oxirane (RS)-4 using lithium bromide to afford a racemic alcohol, 1-chloro-3-(4-(2-methoxyphenyl) piperazin-1-yl) propan-2-ol (RS)-6 in 85% yield. Intermediate (S)-6 was synthesized from racemic alcohol (RS)-6 using Candida rugosa lipase (CRL) with vinyl acetate as the acyl donor. Various reaction parameters such as temperature, time, substrate, enzyme concentration, and the effect of the reaction medium on the conversion and enantiomeric excess for the transesterification of (RS)-6 by CRL were optimized. It was observed that 10 mM of (RS)-6, 50 mg/mL of CRL in 4.0 mL of toluene with vinyl acetate (5.4 mmol) as acyl donor at 30 °C gave good conversion (C = 49.4%) and enantiomeric excess (eeP = 98.4% and eeS = 96%) after 9 h of reaction. Compound (S)-6 is a key intermediate for the synthesis of enantiopure (S)-1. The (RS)- and (S)-enciprazine drug 1 was synthesized by treating (RS)- and (S)-6 with 3,4,5-trimethoxyphenol 5 using MeCN as a solvent and K2CO3 as a base.
1-[3-(3,4,5-Trimethoxyphenoxy)-2-hydroxy-propyl]-4-aryl-piperazine-derivatives having pharmaceutical activity
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, (2008/06/13)
There are prepared compounds corresponding to the general formula STR1 in which R1 is a hydrogen atom, a C2 to C6 -alkanoyl group, a C3 to C6 -alkenoyl group, a C3 to C6 -cycloalkyl carbonyl group, a benzoyl group, an alkoxybenzoyl group, a nicotinoyl group, a thienyl carbonyl group, a furyl carbonyl group, a phenylacetyl group or a C1 to C4 -alkoxyphenyl acetyl group and R2 represents a phenyl, naphthyl or pyridyl group or such group substituted by the groups R3 and R4, the groups R3 and R4, which may be the same or different, each representing hydrogen, hydroxyl, fluorine, chlorine, bromine, a nitro group, a trifluoromethyl group, a C1 to C6 -alkyl group, a C1 to C6 -alkoxy group, a C1 to C6 -alkyl thio group, a C1 to C6 -alkyl sulphonyl group, a C2 to C6 -alkanoyl group, an amino group, an acylamino group or an acyloxy group in which the acyl is of the type defined in respect to R1, and their salts. The compounds are pharmacodynamically active.
