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

HRID 273739Notes

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

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 11026Titanium isopropoxideCatalyst

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
Patent number
US05387593

Reaction notes

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