N-3-Bromopropylphthalimide → 2-[3-(4-Benzhydryl-2,6-cis-dimethylpiperazin-1-yl)-propyl]-isoindole-1,3-dione

HRID 1986172Notes

Reaction equation

HRID 1986172 reaction equation
Br[CH2:2][CH2:3][CH2:4][N:5]1[C:9](=[O:10])[C:8]2=[CH:11][CH:12]=[CH:13][CH:14]=[C:7]2[C:6]1=[O:15].[CH:16]([N:29]1[CH2:34][C@H:33]([CH3:35])[NH:32][C@H:31]([CH3:36])[CH2:30]1)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(N(C(C)C)CC)(C)C>CN(C)C(=O)C>[CH:16]([N:29]1[CH2:30][C@@H:31]([CH3:36])[N:32]([CH2:2][CH2:3][CH2:4][N:5]2[C:9](=[O:10])[C:8]3[C:7](=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:6]2=[O:15])[C@@H:33]([CH3:35])[CH2:34]1)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 21611N-3-BromopropylphthalimideHCID 81531DiisopropylethylamineHCID 68856697Benzhydryl-3,5-cis-dimethylpiperazine

Product 1

HCID 688579152-[3-(4-Benzhydryl-2,6-cis-dimethylpiperazin-1-yl)-propyl]-isoindole-1,3-dione

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

N-(3-Bromopropyl)phthalimide (2.50 g, 9.33 mmol) is added to a stirred solution of benzhydryl-3,5-cis-dimethylpiperazine (2.61 g, 9.33 mmol) and diisopropylethylamine (1.81 g, 14.0 mmol) in N,N-dimethylacetamide (25 mL). The resultant mixture is heated at 120° C. for 48 hours. After concentration and subsequent chromatography on silica gel, eluting with 2 M NH3/CH3OH in dichloromethane: 0-1%, 2-[3-(4-benzhydryl-2,6-cis-dimethylpiperazin-1-yl)-propyl]-isoindole-1,3-dione is obtained as a brown oil (1.98 g, 45% 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-cddc23d5336e4d9d85d2be95d2b030e8
Source dataset
uspto-grants-2009_06
Patent number
US07547691B2

Reaction notes

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