Ammonia → (S)-5,10-Dihydro-5-[[2-[(4-methyl-1-piperazinyl)methyl]-1-pyrrolidinyl]-acetyl]-11H-dibenzo[b,e][1,4]diazepin-11-one

HRID 465078Notes

Reaction equation

HRID 465078 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].[CH3:21][N:22]1[CH2:27][CH2:26][N:25]([CH2:28][C@@H:29]2[CH2:33][CH2:32][CH2:31][NH:30]2)[CH2:24][CH2:23]1.C(OCC)(=O)C.N>ClCCl.CO.C1CCCCC1.C(O)C>[CH3:21][N:22]1[CH2:23][CH2:24][N:25]([CH2:28][C@@H:29]2[CH2:33][CH2:32][CH2:31][N:30]2[CH2:2][C:3]([N:5]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[C:9](=[O:16])[NH:8][C:7]3[CH:17]=[CH:18][CH:19]=[CH:20][C:6]2=3)=[O:4])[CH2:26][CH2:27]1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 8857Ethyl AcetateHCID 100854195-(chloroacetyl)-5,10-dihydro-11H-dibenzo[b,e][1,4]diazepin-11-oneHCID 132751161-Methyl-4-[(2S)-pyrrolidin-2-ylmethyl]piperazine

Product 1

HCID 13578587(S)-5,10-Dihydro-5-[[2-[(4-methyl-1-piperazinyl)methyl]-1-pyrrolidinyl]-acetyl]-11H-dibenzo[b,e][1,4]diazepin-11-one

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 69163855HCID 69163855, compoundSolvent

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-[(4-methyl-1-piperazinyl)methyl]pyrrolidine to give colorless crystals, mp. 168°-170° C. (ethyl acetate). [α]D20 =-18.9° C. (ethanol). RF 0.33 (Merck ready-made TLC plates, silica gel 60 F-254; eluant: dichloromethane/methanol/cyclohexane/conc. ammonia [120:24:30:2]). A second isomer (RF 0.30) can be detected in the mother liquors by thin layer chromatography.

Sources & evidence

ORD record
ord-25c86d84b8c54f70956b41e13059e4d3
Source dataset
uspto-grants-1985_10
Patent number
US04550107

Reaction notes

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