Hydrochloric Acid → (+)-4-[[[2-[2-[(Diethylamino)methyl]-piperidin-l-yl]ethyl]amino]carbonyl]-4,9-dihydro-3-methyl-10H-thieno[3,4-b][1,5]benzodiazepin-10-one

HRID 2351445Notes

Reaction equation

HRID 2351445 reaction equation
Cl[C:2]([N:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[NH:8][C:7](=[O:15])[C:6]2=[CH:16][S:17][C:18]([CH3:19])=[C:5]12)=[O:3].[CH2:20]([N:22]([CH2:25][CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][N:27]1[CH2:32][CH2:33][NH2:34])[CH2:23][CH3:24])[CH3:21].Cl>C(#N)C>[CH2:20]([N:22]([CH2:25][CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][N:27]1[CH2:32][CH2:33][NH:34][C:2]([N:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[NH:8][C:7](=[O:15])[C:6]2=[CH:16][S:17][C:18]([CH3:19])=[C:5]12)=[O:3])[CH2:23][CH3:24])[CH3:21]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 142099804-chlorocarbonyl-4,9-dihydro-3-methyl-10H-thieno[3,4-b][1,5]benzodiazepin-10-oneHCID 142100002-[2-[(Diethylamino)methyl]piperidin-1-yl]ethanamine

Product 1

HCID 14210081(+)-4-[[[2-[2-[(Diethylamino)methyl]-piperidin-l-yl]ethyl]amino]carbonyl]-4,9-dihydro-3-methyl-10H-thieno[3,4-b][1,5]benzodiazepin-10-oneYield 53%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Prepared analogously to Example 1 from 4-(chlorocarbonyl)-4,9-dihydro-3-methyl-10H-thieno[3,4-b][1,5]benzodiazepin-10-one and (-)-2-[2-[(diethylamino)methyl]-piperidin-l-yl]ethanamine in a yield of 53% of theory. Colourless crystals, m.p. 132°-133° C. (acetonitrile); [α]D20 =-14.00° (dilute aqueous hydrochloric acid).

Sources & evidence

ORD record
ord-c82d37877aae497da4c5eec379e5699a
Source dataset
uspto-grants-1989_10
Patent number
US04873236

Reaction notes

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