1,4-Dimethylpiperazine → Pirenzepine

HRID 1981850Notes

Reaction equation

HRID 1981850 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]=[N:20][C:6]1=2)=[O:4].[CH3:21][N:22]1[CH2:27][CH2:26][N:25](C)[CH2:24][CH2:23]1>C(#N)C>[CH3:21][N:22]1[CH2:27][CH2:26][N:25]([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]=[N:20][C:6]2=3)=[O:4])[CH2:24][CH2:23]1

Participants

4

Reactant 2

HCID 78181,4-DimethylpiperazineHCID 12005311-(Chloroacetyl)-5,11-dihydro-6H-pyrido(2,3-b)(1,4)benzodiazepin-6-one

Product 1

HCID 4848PirenzepineYield 49.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 11-(2-chloroacetyl)-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one (5 g) and N,N'-dimethylpiperazine (4 g) in acetonitrile (100 ml) was heated to reflux for 2 hours. The mixture was evaporated and the residue, crystallized from methanol, yielded 3 g (42.9%) of 11-[2-(4-methylpiperazin-1-yl)-acetyl]-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one N1 -chloromethylate melting at 198°-200° C.

Workup

  1. temperatureto reflux for 2 hours
  2. customThe mixture was evaporated
  3. customthe residue, crystallized from methanol

Sources & evidence

ORD record
ord-40acc5e1843f4693a57a9d0559e75357
Source dataset
uspto-grants-1986_06
Patent number
US04594190

Reaction notes

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