Phenethylamine → HCID 11589420, compound

HRID 908965Notes

Reaction equation

HRID 908965 reaction equation
ON1C2C=CC=CC=2N=N1.[C:11]1([CH2:17][CH2:18][NH2:19])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.CN1CCOCC1.Cl.[CH3:28][N:29]([CH3:46])[C:30]1([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH2:35][CH2:34][CH:33]([CH2:36][C:37]([OH:39])=O)[CH2:32][CH2:31]1.C1(N=C=NC2CCCCC2)CCCCC1.[OH-].[Na+]>CN(C)C=O.O>[CH3:46][N:29]([CH3:28])[C:30]1([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH2:31][CH2:32][CH:33]([CH2:36][C:37]([NH:19][CH2:18][CH2:17][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:39])[CH2:34][CH2:35]1

Participants

9

Reactant 6

HCID 1001PhenethylamineHCID 79724-MethylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 14798Sodium HydroxideHCID 757711-HydroxybenzotriazoleHCID 673861314-Dimethylamino-4-phenylcyclohexyl-acetic acid hydrochloride

Product 1

HCID 11589420HCID 11589420, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

1-Hydroxybenzotriazole (273 mg, 2.0 mmol), 2-phenylethylamine (0.125 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 at 0° C. and the mixture was stirred at RT for 5 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). Still further urea thereby precipitated out as a mixture with the product (349 mg) and was separated off. The filtrate obtained was diluted with water (300 ml), 5 M sodium hydroxide solution (8 ml, 40 mmol) was added and the mixture was stored at 5° C. for 16 h. Further product thereby precipitated out as a colourless solid (172 mg). After purification of the fraction contaminated with dicyclohexylurea by chromatography on silica gel with methanol, further product (49 mg) was obtained. The product was isolated in a total yield of 61% (221 mg) with an m.p. of 182-186° C.

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. customStill further urea thereby precipitated out as a mixture with the product (349 mg)
  5. customwas separated off
  6. customThe filtrate obtained
  7. additionwas added
  8. waitthe mixture was stored at 5° C. for 16 h
  9. customFurther product thereby precipitated out as a colourless solid (172 mg)
  10. customAfter purification of the fraction

Sources & evidence

ORD record
ord-02723f40790c4e21835f235eb41b9d79
Source dataset
uspto-grants-2011_09
Patent number
US08017630B2

Reaction notes

Loading…