Water → (2R)-4-benzyl-2-[4-chloro-3-(tert-butyldimethylsilyloxy)benzyl]piperazine

HRID 1374997Notes

Reaction equation

HRID 1374997 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][C@@H:7]2[CH2:12][N:11]([CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:10][CH2:9][NH:8]2)=[CH:4][C:3]=1[OH:22].C(N(CC)CC)C.[Si:30](Cl)([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31].O>ClCCl.CN(C)C1C=CN=CC=1>[CH2:13]([N:11]1[CH2:10][CH2:9][NH:8][C@H:7]([CH2:6][C:5]2[CH:20]=[CH:21][C:2]([Cl:1])=[C:3]([O:22][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])[CH:4]=2)[CH2:12]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 54261549(2R)-2-(4-chloro-3-hydroxybenzyl)-4-benzylpiperazine

Product 1

HCID 54436042(2R)-4-benzyl-2-[4-chloro-3-(tert-butyldimethylsilyloxy)benzyl]piperazineYield 79.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (2R)-2-(4-chloro-3-hydroxybenzyl)-4-benzylpiperazine (3.78 g) and triethylamine (5.71 ml) in dichloromethane was added 4-dimethylaminopyridine (0.29 g) and tert-butyldimethylsilyl chloride (5.30 g) successively with ice bath cooling under nitrogen atmosphere. After stirring overnight at room temperature, water (50 ml) was added to the mixture and the organic layer was separated, washed with brine, dried over sodium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel with a mixture of dichloromethane and methanol (10:1) as eluent to give (2R)-4-benzyl-2-[4-chloro-3-(tert-butyldimethylsilyloxy)benzyl]piperazine (4.11 g) as an oil.

Workup

  1. temperaturecooling under nitrogen atmosphere
  2. customthe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by column chromatography on silica gel with a mixture of dichloromethane and methanol (10:1) as eluent

Sources & evidence

ORD record
ord-fb3029d8fe83458faaac2560f2980618
Source dataset
uspto-grants-2007_01
Patent number
US07166598B2

Reaction notes

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