HCID 14209978, compound → HCID 14210049, compound

HRID 2351400Notes

Reaction equation

HRID 2351400 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([C:12](Cl)=[O:13])[C:10]3[N:15]=[CH:16][CH:17]=[CH:18][C:9]=3[NH:8][C:7](=[O:19])[C:6]=2[CH:20]=1.[CH2:21]([N:23]([CH2:26][CH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][N:28]1[CH2:33][CH2:34][NH2:35])[CH2:24][CH3:25])[CH3:22]>ClCCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([C:12]([NH:35][CH2:34][CH2:33][N:28]3[CH2:29][CH2:30][CH2:31][CH2:32][CH:27]3[CH2:26][N:23]([CH2:21][CH3:22])[CH2:24][CH3:25])=[O:13])[C:10]3[N:15]=[CH:16][CH:17]=[CH:18][C:9]=3[NH:8][C:7](=[O:19])[C:6]=2[CH:20]=1

Participants

4

Reactant 2

HCID 14209978HCID 14209978, compoundHCID 142100002-[2-[(Diethylamino)methyl]piperidin-1-yl]ethanamine

Product 1

HCID 14210049HCID 14210049, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 3.1 g (0.01 mol) of 8-chloro-11-(chlorocarbonyl)-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one, 2.6 g (0.0122 mol) of 2-[2-[(diethylamino)methy]-piperidin-1-yl]ethanamine and 310 ml of 1,2-dichloroethane was stirred for 21/2 hours at ambient temperature, then extracted exhaustively with dilute hydrochloric acid. The combined aqueous extracts were made alkaline with saturated aqueous potassium carbonate solution and extracted exhaustively with dichloromethane. The dichloromethane phases were combined, dried over sodium sulphate with the addition of 1 g of animal charcoal and evaporated down in vacuo. After being triturated with diisopropylether the oily residue became crystalline and was recrystallised from acetonitrile. 2.9 g (60% of theory) of colourless crystals were obtained, m.p. 138°-140° C.

Workup

  1. extractionextracted exhaustively with dilute hydrochloric acid
  2. extractionextracted exhaustively with dichloromethane
  3. dry with materialdried over sodium sulphate with the addition of 1 g of animal charcoal
  4. customevaporated down in vacuo
  5. customAfter being triturated with diisopropylether the oily residue
  6. customwas recrystallised from acetonitrile
  7. custom2.9 g (60% of theory) of colourless crystals were obtained

Sources & evidence

ORD record
ord-95d623947a9c4f0b9f0eeaf4c3a8bc20
Source dataset
uspto-grants-1989_10
Patent number
US04873236

Reaction notes

Loading…