Triethylamine → HCID 19607912, compound

HRID 1291641Notes

Reaction equation

HRID 1291641 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-61e19e43342e41cabab5cb19db783b78
Source dataset
uspto-grants-1998_05
Patent number
US05753677

Reaction notes

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