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

HRID 2260504
Notes
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Reaction equation

HRID 2260504 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-61d3c8aca349440896fe77e84e85200b
Source dataset
uspto-grants-1995_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05478828

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes