Phenethylamine → HCID 9893094, compound

HRID 2305220Notes

Reaction equation

HRID 2305220 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([C@@H:18]3[CH2:22][CH2:21][CH2:20][C@H:19]3[CH2:23][C:24]3[CH:25]=[C:26]([CH:30]=[CH:31][CH:32]=3)[C:27]([OH:29])=O)[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:33]1([CH2:39][CH2:40][NH2:41])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.Cl.C(N=C=NCCCN(C)C)C>CN(C=O)C.CCOC(C)=O>[C:33]1([CH2:39][CH2:40][NH:41][C:27](=[O:29])[C:26]2[CH:30]=[CH:31][CH:32]=[C:24]([CH2:23][C@@H:19]3[CH2:20][CH2:21][CH2:22][C@H:18]3[C:9]3[O:10][C:11]([C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=4)=[C:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[N:8]=3)[CH:25]=2)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

6

Reactant 3

HCID 1001PhenethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 11327698HCID 11327698, compound

Product 1

HCID 9893094HCID 9893094, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 3-{[(1S,2R)-2-(4,5-diphenyloxazol-2-yl)-1-cyclopentyl]methyl}benzoic acid (140 mg, 0.331 mmol) and 2-phenylethylamine (0.046 ml, 0.364 mmol) in DMF (5 ml) was added 1-hydroxybenzotrioxazole (49 mg, 0.364 mmol) and 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (95 mg, 0.495 mmol). After stirring the mixture at room temperature for 2.5 hours, the reaction mixture was diluted with EtOAc (30 ml), washed with water, saturated sodium hydrogencarbonate solution, water, and brine. The resultant mixture was dried over magnesium sulfate, and evaporated in vacuo. The resultant residue was purified by silica gel column chromatography (hexane:EtOAc, 2:1 elution) to give N-(2-phenylethyl)-3-{[(1S,2R)-2-(4,5-diphenyloxazol-2-yl)-1-cyclopentyl]methyl}benzamide (172.1 mg, 99%).

Workup

  1. washwashed with water, saturated sodium hydrogencarbonate solution, water, and brine
  2. dry with materialThe resultant mixture was dried over magnesium sulfate
  3. customevaporated in vacuo
  4. customThe resultant residue was purified by silica gel column chromatography (hexane:EtOAc, 2:1 elution)

Sources & evidence

ORD record
ord-1b57ebda1f5b49ef889fedab496d9fb4
Source dataset
uspto-grants-2002_08
Patent number
US06437146B1

Reaction notes

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