Ethyl Acetate → Ammonia methanol

HRID 1350508Notes

Reaction equation

HRID 1350508 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].[F:20][C:21]1[CH:22]=[C:23]([CH2:27][CH2:28][C@H:29]2[CH2:34]N[CH2:32][CH2:31][NH:30]2)[CH:24]=[CH:25][CH:26]=1.[C:35](OCC)(=[O:37])C>C1(C)C=CC=CC=1.CS(C)=O>[NH3:8].[CH3:35][OH:37].[F:20][C:21]1[CH:22]=[C:23]([CH2:27][CH2:28][C@@H:29]2[NH:30][CH2:31][CH2:32][N:13]([C:12]3[C:6]4[CH:5]=[C:4]([CH:1]([CH3:3])[CH3:2])[CH:19]=[CH:18][C:7]=4[NH:8][C:9]4[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=4[N:11]=3)[CH2:34]2)[CH:24]=[CH:25][CH:26]=1

Participants

7

Reactant 3

HCID 8857Ethyl AcetateHCID 210934852-isopropyl-5H-dibenzo[b,e][1,4]diazepin-11-ylamineHCID 21093648(S)-2-(2-(3-Fluoro-phenyl)-ethyl)-piperazine

Product 2

HCID 21705897Ammonia methanolHCID 58860718(S)-11-{3-[2-(3-Fluoro-phenyl)-ethyl]-piperazin-1-yl}-2-isopropyl-5H-dibenzo[b,e][1,4]diazepine

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 1140TolueneSolvent

Procedure

Combine 2-isopropyl-5H-dibenzo[b,e][1,4]diazepin-11-ylamine (0.665 g, 2.31 mmol) and (S)-2-[2-(3-fluoro-phenyl)-ethyl]-piperazine (0.962 g, 4.62 mmol)in toluene (4.0 mL) and DMSO (1.0 mL) and heat at 110° C. for 18 hours. Cool to ambient temperature and dilute with ethyl acetate (75 mL). Wash with 0.1N NaOH solution, water and evaporate to give 0.996 g of the crude product. Silica gel chromatography, eluting with methylene chloride: 2N NH3/methanol (100:4), gives 0.216 g of the title compound as a tan solid: mass spectrum (ion spray): n/z=443 (M+1).

Workup

  1. washWash with 0.1N NaOH solution, water
  2. customevaporate
  3. customto give 0.996 g of the crude product
  4. washSilica gel chromatography, eluting with methylene chloride

Sources & evidence

ORD record
ord-eab96f954eba436ca00721b45940792c
Source dataset
uspto-grants-2007_05
Patent number
US07214673B2

Reaction notes

Loading…