Triethylamine → 11-(2-(2-((Diethylamino)methyl)-1-piperidinyl)acetyl)-5,11-dihydro-6H-pyrido(2,3-b)(1,4)benzodiazepin-6-one

HRID 465081

Reaction equation

C(Cl)(=O)[O:2][CH2:3][CH3:4].[N:7]1[C:12]2[NH:13][C:14]3[CH:22]=[CH:21][CH:20]=[CH:19][C:15]=3[C:16](=[O:18])[NH:17][C:11]=2[CH:10]=[CH:9][CH:8]=1.[CH2:23]([N:25]([CH2:28][CH3:29])[CH2:26][CH3:27])[CH3:24].[OH-].[Na+]>O1CCCC1>[CH2:23]([N:25]([CH2:28][CH:29]1[CH2:11][CH2:10][CH2:9][CH2:8][N:7]1[CH2:4][C:3]([N:13]1[C:14]2[CH:22]=[CH:21][CH:20]=[CH:19][C:15]=2[C:16](=[O:18])[NH:17][C:11]2[CH:10]=[CH:9][CH:8]=[N:7][C:12]1=2)=[O:2])[CH2:26][CH3:27])[CH3:24]

Participants

Conditions

Temperature: 0 °C

Procedure

Ethyl chlorocarbonate (11.0 g, 0.101 mol) is added dropwise, at 0° C., to a suspension of 2-[(diethylamino)methyl]-1-piperidino acetic acid (22.83 g, 0.1 mol) in dry tetrahydrofuran (200 ml). Then, 5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one (21.12 g, 0.1 mol) and triethylamine (20.24 g, 0.2 mol) are added to the resulting suspension which is then stirred for a further hour at 0° C. and then for 4 hours at ambient temperature. The mixture is poured into 2N sodium hydroxide solution (1.6 liters), extracted exhaustively with dichloromethane, the organic phase concentrated to dryness and the residue purified by recrystallization from ethanol and from methanol. Colorless crystals (6.3 g) are obtained, mp. 226°-228° C., which were shown by thin layer chromatography, mixed melting point and IR spectrum to be identical to a sample prepared according to Example 34.

Workup

extractionextracted exhaustively with dichloromethane
concentrationthe organic phase concentrated to dryness
customthe residue purified by recrystallization from ethanol and from methanol

Sources & evidence

ORD record: ord-901753c25af7418f9c10fcb008b79f6c
Source dataset: uspto-grants-1985_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04550107

Linked notes

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