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Benzyl piperazine-1-carboxylate → Phenylmethyl [4-(4-fluorophenyl)-4-methoxy-1-cyclohexyl]-1-piperazinecarboxylate

HRID 273739
Notes
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Reaction equation

HRID 273739 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([O:15][CH3:16])[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[N:17]1([C:23]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:24])[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.[BH4-].[Na+]>CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([O:15][CH3:16])[CH2:13][CH2:12][CH:11]([CH:18]3[CH2:19][NH:20][CH2:21][CH2:22][N:17]3[C:23]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[O:24])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 643495Benzyl piperazine-1-carboxylateHCID 4311764Sodium borohydrideHCID 184002134-(4-Fluorophenyl)-4-methoxycyclohexanone

Product 1

HCID 86748438Phenylmethyl [4-(4-fluorophenyl)-4-methoxy-1-cyclohexyl]-1-piperazinecarboxylateYield 35.7%

Reagents, catalysts & solvents 1

HCID 11026
Titanium isopropoxide
Catalyst

Procedure

A mixture of 4-(4-fluorophenyl)-4-methoxycyclohexanone (2,2 g, 10 mmole), phenylmethyl 1-piperazinecarboxylate (2.2 g, 10 mmole), titanium(IV) isopropoxide (3.7 ml, 11 mmole) were mixed, reacted and reduced with sodium borohydride (0.4 g, 10 mmole) as in example 5. The crude product was purified by chromatography on silica eluting with methanol-methylene chloride (1:50) to give phenylmethyl [4-(4-fluorophenyl)-4-methoxy-1-cyclohexyl]-1-piperazinecarboxylate (35.7%, mp: 68°-69° C.).

Workup

  1. additionwere mixed
  2. customreacted
  3. customThe crude product was purified by chromatography on silica eluting with methanol-methylene chloride (1:50)

Sources & evidence

ORD record
ord-c555c7d6bdc449958efda9ced2121a94
Source dataset
uspto-grants-1995_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05387593

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes