4-Methylmorpholine → 2-chloro-N-(4-(((2-hydroxy-1-phenylpropyl)amino)carbonyl)phenyl)benzamide

HRID 1951582Notes

Reaction equation

HRID 1951582 reaction equation
CN1CCOCC1.ON1C2C=CC=CC=2N=N1.[NH2:18][CH:19]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH:20]([OH:22])[CH3:21].[Cl:29][C:30]1[CH:47]=[CH:46][CH:45]=[CH:44][C:31]=1[C:32]([NH:34][C:35]1[CH:43]=[CH:42][C:38]([C:39](O)=[O:40])=[CH:37][CH:36]=1)=[O:33].Cl.CN(C)CCCN=C=NCC>CN(C=O)C.C(OCC)(=O)C.O>[Cl:29][C:30]1[CH:47]=[CH:46][CH:45]=[CH:44][C:31]=1[C:32]([NH:34][C:35]1[CH:43]=[CH:42][C:38]([C:39]([NH:18][CH:19]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:20]([OH:22])[CH3:21])=[O:40])=[CH:37][CH:36]=1)=[O:33]

Participants

9

Reactant 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 11329884-(2-Chlorobenzamido)benzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 123529221-Amino-1-phenylpropan-2-ol

Product 1

HCID 574653742-chloro-N-(4-(((2-hydroxy-1-phenylpropyl)amino)carbonyl)phenyl)benzamide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

to a room temperature mixture of 1-methylmorpholine (602 mg, 5.95 mmol), 1-hydroxybenzotriazole (322 mg, 2.38 mmol), 1-amino-1-phenylpropan-2-ol (300 mg, 1.98 mmol) and 4-(2-chlorobenzamido)benzoic acid (656 mg, 2.38 mmol) dissolved in 10 mL DMF was added N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (456 mg, 2.38 mmol) all in one portion. The reaction was left to stir at ambient temperature for 20 hours then poured into 30 mL water. The aqueous mixture was extracted with 50 mL 30% dichloromethane in diethyl ether. The organic extract was washed with 3×25 mL water then 20 mL brine, stirred over magnesium sulfate, filtered and the filtrate concentrated under reduced pressure to afford a white solid. The solid was suspended in hot ethyl acetate, cooled to room temperature and filtered, drying over a stream of air (658 mg, 81%). ESI+ m/z=409.1 [MH]+.

Workup

  1. waitThe reaction was left
  2. extractionThe aqueous mixture was extracted with 50 mL 30% dichloromethane in diethyl ether
  3. extractionThe organic extract
  4. washwas washed with 3×25 mL water
  5. stirring20 mL brine, stirred over magnesium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated under reduced pressure
  8. customto afford a white solid
  9. temperaturecooled to room temperature
  10. filtrationfiltered
  11. customdrying over a stream of air (658 mg, 81%)

Sources & evidence

ORD record
ord-597591de38454278973aa19458e72d93
Source dataset
uspto-grants-2013_03
Patent number
US08404722B2

Reaction notes

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