Triethylamine → HCID 19607912, compound

HRID 745079Notes

Reaction equation

HRID 745079 reaction equation
[C:1]([CH2:4][O:5][CH:6]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]([C:17](=[O:34])[C:18]2[CH:23]=[CH:22][C:21]([NH:24][C:25](=[O:33])[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[CH3:32])=[CH:20][CH:19]=2)[CH2:9][CH2:8][CH2:7]1)(O)=[O:2].Cl.[CH3:36][NH:37][CH3:38].P(Cl)(OCC)(OCC)=O.C(N(CC)CC)C>CN(C)C=O.O>[CH3:36][N:37]([CH3:38])[C:1]([CH2:4][O:5][CH:6]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]([C:17](=[O:34])[C:18]2[CH:19]=[CH:20][C:21]([NH:24][C:25](=[O:33])[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[CH3:32])=[CH:22][CH:23]=2)[CH2:9][CH2:8][CH2:7]1)=[O:2]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 13139Diethyl chlorophosphateHCID 19607815HCID 19607815, compound

Product 1

HCID 19607912HCID 19607912, compoundYield 85.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

5-Carboxymethoxy-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.55 g) is dissolved in dimethylformamide (20 ml) and thereto are added dimethylamine hydrochloride (0.20 g) and diethyl chlorophosphate (0.33 g). To the mixture is added triethylamine (1.0 ml) under ice-cooling, and the mixture is stirred under ice-cooling for 30 minutes, and at room temperature for more 2 hours. Water is added to the reaction solution and the precipitated crystal is collected by filtration and recrystallized from ethyl acetate/n-hexane to give 5-dimethylaminocarbonylmethoxy-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.50 g) as colorless prisms, m.p. 203°-204° C.

Workup

  1. temperaturecooling
  2. temperaturecooling for 30 minutes
  3. filtrationthe precipitated crystal is collected by filtration
  4. customrecrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-055f6b00c13d43c99790774ef18fe6bd
Source dataset
uspto-grants-1996_09
Patent number
US05559230

Reaction notes

Loading…