Potassium Carbonate → 2-[(4-Chloro-benzyl)-(1-{3-[7-(1-hydroxy-1-methyl-ethyl)-11H-10-oxa-1-aza-dibenzo[a,d]cyclohepten-5-ylidene]-propyl}-pyrrolidin-3-yl)-amino]-N-ethyl-acetamide

HRID 917220Notes

Reaction equation

HRID 917220 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][N:7]([CH:14]2[CH2:18][CH2:17][NH:16][CH2:15]2)[CH2:8][C:9]([NH:11][CH2:12][CH3:13])=[O:10])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:28][CH2:29]/[CH:30]=[C:31]1/[C:32]2[CH:45]=[C:44]([C:46]([OH:49])([CH3:48])[CH3:47])[CH:43]=[CH:42][C:33]=2[O:34][CH2:35][C:36]2[N:41]=[CH:40][CH:39]=[CH:38][C:37]/1=2>C(#N)C.O>[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][N:7]([CH:14]2[CH2:18][CH2:17][N:16]([CH2:28][CH2:29][CH:30]=[C:31]3[C:37]4[CH:38]=[CH:39][CH:40]=[N:41][C:36]=4[CH2:35][O:34][C:33]4[CH:42]=[CH:43][C:44]([C:46]([OH:49])([CH3:48])[CH3:47])=[CH:45][C:32]3=4)[CH2:15]2)[CH2:8][C:9]([NH:11][CH2:12][CH3:13])=[O:10])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 23136844(E)-2-[5-(3-bromo-propylidene)-5,11-dihydro-10-oxa-1-aza-dibenzo[a,d]cyclohepten-7-yl]-propan-2-olHCID 231370142-[(4-chloro-benzyl)-pyrrolidin-3-yl-amino]-N-ethyl-acetamide

Product 1

HCID 667587462-[(4-Chloro-benzyl)-(1-{3-[7-(1-hydroxy-1-methyl-ethyl)-11H-10-oxa-1-aza-dibenzo[a,d]cyclohepten-5-ylidene]-propyl}-pyrrolidin-3-yl)-amino]-N-ethyl-acetamide

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2-[(4-chloro-benzyl)-pyrrolidin-3-yl-amino]-N-ethyl-acetamide (0.09 g, 0.31 mmol) in acetonitrile:water (4:1) was added potassium carbonate (0.07 g, 0.51 mmol) and (E)-2-[5-(3-bromo-propylidene)-5,11-dihydro-10-oxa-1-aza-dibenzo[a,d]cyclohepten-7-yl]-propan-2-ol (0.095 g, 0.25 mmol) and the resulting mixture was stirred at 50° C. for 24 h. The reaction mixture was concentrated in vacuo, diluted with ethyl acetate, and dried over sodium sulfate.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additiondiluted with ethyl acetate
  3. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-3f0329b8b599435eafbdc423edebdcfc
Source dataset
uspto-grants-2007_09
Patent number
US07271176B2

Reaction notes

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