2-isopropyl-5H-dibenzo[b,e][1,4]diazepin-11-ylamine → (S)-2-Isopropyl-11-[3-(2-methoxy-ethyl)-piperazin-1-yl]-5H-dibenzo[b,e][1,4]diazepine

HRID 131418Notes

Reaction equation

HRID 131418 reaction equation
[CH:1]([C:4]1[CH:19]=[CH:18][C:7]2[NH:8][C:9]3[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=3[N:11]=[C:12]([NH2:13])[C:6]=2[CH:5]=1)([CH3:3])[CH3:2].[CH3:20][O:21][CH2:22][CH2:23][C@H:24]1[CH2:29]N[CH2:27][CH2:26][NH:25]1>CN1C(=O)CCC1.O>[NH3:8].[CH3:20][OH:21].[CH:1]([C:4]1[CH:19]=[CH:18][C:7]2[NH:8][C:9]3[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=3[N:11]=[C:12]([N:13]3[CH2:27][CH2:26][NH:25][C@@H:24]([CH2:23][CH2:22][O:21][CH3:20])[CH2:29]3)[C:6]=2[CH:5]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 2

HCID 210934852-isopropyl-5H-dibenzo[b,e][1,4]diazepin-11-ylamineHCID 55287560(S)-2-(2-Methoxyethyl)piperazine

Product 2

HCID 10249082(S)-2-Isopropyl-11-[3-(2-methoxy-ethyl)-piperazin-1-yl]-5H-dibenzo[b,e][1,4]diazepineYield 76.9%HCID 21705897Ammonia methanol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Combine 2-Isopropyl-5H-dibenzo[b,e][1,4]diazepin-11-ylamine (0.969 g, 3.85 mmol) and (S)-2-(2-methoxy-ethyl)-piperazine (0.556 g, 3.85 mmol) in NMP (7.0 mL) and heat at 200° C. for 4 hours. Cool to ambient temperature and dilute with water. Extract with ethyl acetate to give 1.51 g of the crude product. Silica gel chromatography, eluting with methylene chloride: 2N NH3/methanol (100:4), gives 0.560 g of the title compound as a tan solid: mp=158-160° C.; mass spectrum (ion spray): m/z=379 (M+1); Analysis for C23H30N4O(0.2H2O): calcd: C, 72.29; H, 8.02; N, 14.66; found: C, 72.20; H, 7.70; N, 14.60.

Workup

  1. extractionExtract with ethyl acetate
  2. customto give 1.51 g of the crude product
  3. washSilica gel chromatography, eluting with methylene chloride

Sources & evidence

ORD record
ord-f0efd4b5b683445b99098a110d165b32
Source dataset
uspto-grants-2008_06
Patent number
US07384934B2

Reaction notes

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