Triethylamine → HCID 20261503, compound

HRID 465080Notes

Reaction equation

HRID 465080 reaction equation
[Cl:1][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].Cl.[CH3:22][N:23]([CH3:30])[CH:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1.C(N(CC)CC)C>O1CCOCC1>[ClH:1].[CH3:22][N:23]([CH3:30])[CH:24]1[CH2:29][CH2:28][N:27]([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])[CH2:26][CH2:25]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12005311-(Chloroacetyl)-5,11-dihydro-6H-pyrido(2,3-b)(1,4)benzodiazepin-6-oneHCID 223491904-Piperidinamine, N,N-dimethyl-, hydrochloride (1:1)

Product 1

HCID 20261503HCID 20261503, compoundYield 19.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

First, 11-(chloroacetyl)-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one (7.0 g, 0.0243 mol) is suspended in anhydrous dioxan (150 ml) and refluxed for 3 hours after the addition of 4-(dimethylamino)piperidine hydrochloride (4.9 g, 0.0298 mol) and triethylamine (10.0 g, 0.099 mol). Then the mixture is concentrated in vacuo. The residue is made alkaline with sodium hydroxide and extracted exhaustively with dichloromethane. The combined dichloromethane extracts are dried over sodium sulphate and concentrated. The highly viscous residue is taken up in dioxan, clarified with activated charcoal and mixed with ethereal hydrochloric acid solution. The colorless crystals (2.0 g) obtained melted 258° C. after recrystallization from methanol.

Workup

  1. temperaturerefluxed for 3 hours
  2. concentrationThen the mixture is concentrated in vacuo
  3. extractionextracted exhaustively with dichloromethane
  4. dry with materialThe combined dichloromethane extracts are dried over sodium sulphate
  5. concentrationconcentrated
  6. additionmixed with ethereal hydrochloric acid solution

Sources & evidence

ORD record
ord-fc69290c8fc245c3b6567e53cd213bb5
Source dataset
uspto-grants-1985_10
Patent number
US04550107

Reaction notes

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