Dichloromethane → 4-[[2-[2-[[2-(Diethylamino)ethyl]methylamino]ethyl]-1-piperidinyl]carbonyl]-4,9-dihydro-3-methyl-10H-thieno[3,4-b][1,5]benzodiazepin-10-one

HRID 2106708Notes

Reaction equation

HRID 2106708 reaction equation
ClCCl.Cl[C:5]([N:7]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[NH:11][C:10](=[O:18])[C:9]2=[CH:19][S:20][C:21]([CH3:22])=[C:8]12)=[O:6].[CH2:23]([N:25]([CH2:38][CH3:39])[CH2:26][CH2:27][N:28]([CH3:37])[CH2:29][CH2:30][CH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][NH:32]1)[CH3:24]>C(#N)C>[CH2:38]([N:25]([CH2:23][CH3:24])[CH2:26][CH2:27][N:28]([CH3:37])[CH2:29][CH2:30][CH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][N:32]1[C:5]([N:7]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[NH:11][C:10](=[O:18])[C:9]2=[CH:19][S:20][C:21]([CH3:22])=[C:8]12)=[O:6])[CH3:39]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 142099804-chlorocarbonyl-4,9-dihydro-3-methyl-10H-thieno[3,4-b][1,5]benzodiazepin-10-oneHCID 150573222-[2-[[2-(Diethylamino)ethyl]methylamino]ethyl]piperidine

Product 1

HCID 150573464-[[2-[2-[[2-(Diethylamino)ethyl]methylamino]ethyl]-1-piperidinyl]carbonyl]-4,9-dihydro-3-methyl-10H-thieno[3,4-b][1,5]benzodiazepin-10-oneYield 22%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Prepared analogously to Example 4, but using dichloromethane instead of acetonitrile as solvent, from 4-(chlorocarbonyl)-4,9-dihydro-3-methyl-10H-thieno[3,4-b][1,5]benzodiazepin-10-one and 2-[2-[[2-(diethylamino)ethyl]methylamino]ethyl]piperidine (b.p.0.3 mmHg 92°-95° C.) in a yield of 22% of theory. Colourless crystals, m.p. 131°-133° C. (acetonitrile).

Workup

  1. customPrepared analogously to Example 4

Sources & evidence

ORD record
ord-a6ad5e2da69546eea099c2f53aff027e
Source dataset
uspto-grants-1990_06
Patent number
US04931436

Reaction notes

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