4-Methylmorpholine → HCID 11517238, compound

HRID 908964Notes

Reaction equation

HRID 908964 reaction equation
ON1C2C=CC=CC=2N=N1.[C:11]1([CH2:17][CH2:18][CH2:19][NH2:20])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.CN1CCOCC1.Cl.[CH3:29][N:30]([CH3:47])[C:31]1([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH2:36][CH2:35][CH:34]([CH2:37][C:38](O)=[O:39])[CH2:33][CH2:32]1.C1(N=C=NC2CCCCC2)CCCCC1.[OH-].[Na+]>CN(C)C=O.O.C(O)C>[CH3:47][N:30]([CH3:29])[C:31]1([C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=2)[CH2:36][CH2:35][CH:34]([CH2:37][C:38]([NH:20][CH2:19][CH2:18][CH2:17][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:39])[CH2:33][CH2:32]1

Participants

10

Reactant 6

HCID 79724-MethylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 14798Sodium HydroxideHCID 162593-PhenylpropylamineHCID 757711-HydroxybenzotriazoleHCID 673861314-Dimethylamino-4-phenylcyclohexyl-acetic acid hydrochloride

Product 1

HCID 11517238HCID 11517238, compoundYield 58%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

1-Hydroxybenzotriazole (273 mg, 2.0 mmol), 3-phenylpropylamine (0.142 ml, 1.0 mmol) and N-methylmorpholine (0.222 ml, 2.0 mmol) were added to a solution of (4-dimethylamino-4-phenylcyclohexyl)acetic acid hydrochloride (298 mg, 1.0 mmol) in dry dimethylformamide under argon. Dicyclohexylcarbodiimide (417 mg, 2.0 mmol) was added to the clear solution at 0° C. The reaction mixture was stirred at RT for 3 d, the urea which had precipitated out was filtered off with suction and the filtrate was introduced into a mixture of saturated NaCl solution (40 ml) and saturated NaHCO3 solution (10 ml). 5 M sodium hydroxide solution (12 ml, 60 mmol) was added to the aqueous phase and the mixture was diluted with water (300 ml) and stored at 5° C. for 3 d. The product was thereby produced as a colourless compound and was to be obtained in a yield of 58% (220 mg) by filtration, taking up of the residue in ethanol and concentration.

Workup

  1. customthe urea which had precipitated out
  2. filtrationwas filtered off with suction
  3. additionthe filtrate was introduced into a mixture of saturated NaCl solution (40 ml) and saturated NaHCO3 solution (10 ml)
  4. waitstored at 5° C. for 3 d
  5. customThe product was thereby produced as a colourless compound
  6. customto be obtained in a yield of 58% (220 mg) by filtration
  7. concentrationconcentration

Sources & evidence

ORD record
ord-16d7fd7d4342463eb3f8fc47cc4dc58a
Source dataset
uspto-grants-2011_09
Patent number
US08017630B2

Reaction notes

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