(S)-N-Ethyl-N-(pyrrolidin-2-ylmethyl)ethanamine → (S)-5-[[2-[(Diethylamino)methyl]-1-pyrrolidinyl]acetyl]-5,10-dihydro-11H-dibenzo[b,e][1,4]diazepin-11-one

HRID 465077Notes

Reaction equation

HRID 465077 reaction equation
Cl[CH2:2][C:3]([N:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[C:9](=[O:16])[NH:8][C:7]2[CH:17]=[CH:18][CH:19]=[CH:20][C:6]1=2)=[O:4].[CH2:21]([N:23]([CH2:26][C@@H:27]1[CH2:31][CH2:30][CH2:29][NH:28]1)[CH2:24][CH3:25])[CH3:22]>C(O)C>[CH2:21]([N:23]([CH2:26][C@@H:27]1[CH2:31][CH2:30][CH2:29][N:28]1[CH2:2][C:3]([N:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[C:9](=[O:16])[NH:8][C:7]2[CH:17]=[CH:18][CH:19]=[CH:20][C:6]1=2)=[O:4])[CH2:24][CH3:25])[CH3:22]

Participants

4

Reactant 2

HCID 7141622(S)-N-Ethyl-N-(pyrrolidin-2-ylmethyl)ethanamineHCID 100854195-(chloroacetyl)-5,10-dihydro-11H-dibenzo[b,e][1,4]diazepin-11-one

Product 1

HCID 13578585(S)-5-[[2-[(Diethylamino)methyl]-1-pyrrolidinyl]acetyl]-5,10-dihydro-11H-dibenzo[b,e][1,4]diazepin-11-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The title compound is prepared analogously to Example 31 from 5-(chloroacetyl)-5,10-dihydro-11H-dibenzo[b,e][1,4]diazepin-11-one and (S)-(+)-2-[(diethylamino)methyl]pyrrolidine to give a colorless highly viscous oil, [α]D20 =-10.5° (ethanol).

Sources & evidence

ORD record
ord-d9e522477ed04c76bc624096a37eb099
Source dataset
uspto-grants-1985_10
Patent number
US04550107

Reaction notes

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