Diisopropylethylamine → Benzhydryl-3,5-cis-dimethylpiperazine

HRID 1986171Notes

Reaction equation

HRID 1986171 reaction equation
[CH:1](Br)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:15][C@H:16]1[CH2:21][NH:20][CH2:19][C@@H:18]([CH3:22])[NH:17]1.C(N(C(C)C)CC)(C)C>ClCCl>[CH:1]([N:20]1[CH2:19][C@H:18]([CH3:22])[NH:17][C@H:16]([CH3:15])[CH2:21]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 236603BromodiphenylmethaneHCID 6950261rel-(2R,6S)-2,6-dimethylpiperazine

Product 1

HCID 68856697Benzhydryl-3,5-cis-dimethylpiperazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzhydryl bromide (4.33 g, 17.5 mmol) is added to s stirred solution of 2,6-cis-dimethylpiperazine (2.00 g, 17.5 mmol) and diisopropylethylamine (2.94 g, 22.8 mmol) in anhydrous dichloromethane (50 mL) at 0° C. The resultant mixture is allowed to stir overnight. After concentration and subsequent chromatography on silica gel, eluting with 2 M NH3/CH3OH in dichloromethane: 1-3%, benzhydryl-3,5-cis-dimethyl-piperazine is obtained as a white solid (3.0 g, 61% yield).

Workup

  1. concentrationAfter concentration and subsequent chromatography on silica gel
  2. washeluting with 2 M NH3/CH3OH in dichloromethane

Sources & evidence

ORD record
ord-59795178740346478c426f816bc9ee0d
Source dataset
uspto-grants-2009_06
Patent number
US07547691B2

Reaction notes

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