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Phenethylamine → HCID 9808232, compound

HRID 2305240
Notes
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Reaction equation

HRID 2305240 reaction equation
[C:1]1([CH2:7][CH2:8][NH2:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[C:17]1([C:23]2[N:24]=[C:25]([C:34]3[CH:35]([CH2:40][C:41]4[CH:42]=[C:43]([S:47](Cl)(=[O:49])=[O:48])[CH:44]=[CH:45][CH:46]=4)[CH2:36][CH2:37][CH2:38][CH:39]=3)[O:26][C:27]=2[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(Cl)Cl.CCOC(C)=O>[C:17]1([C:23]2[N:24]=[C:25]([C:34]3[CH:35]([CH2:40][C:41]4[CH:42]=[C:43]([S:47]([NH:9][CH2:8][CH2:7][C:1]5[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=5)(=[O:49])=[O:48])[CH:44]=[CH:45][CH:46]=4)[CH2:36][CH2:37][CH2:38][CH:39]=3)[O:26][C:27]=2[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 1001PhenethylamineHCID 8471TriethylamineHCID 18459146HCID 18459146, compound

Product 1

HCID 9808232HCID 9808232, compoundYield 22%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×
HCID 8857
Ethyl Acetate
Solvent

Procedure

To a solution of 2-phenylethylamine (0.082 ml, 0.65 mmol) and triethylamine (0.097 ml, 0.70 mmol) in methylene chloride (3 ml) was added a solution of crude 3-{[2-(4,5-diphenyloxazol-2-yl)-2-cyclohexen-1-yl]methyl}benzenesulfonyl chloride (213 mg, 0.44 mmol) in methylene chloride (3 ml) at 5° C. After stirring at room temperature for 1 hour, the reaction mixture was diluted with EtOAc, washed with 1N hydrochloric acid, water, saturated sodium hydrogencarbonate solution, water and brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by silica gel column chromatography (hexane:EtOAc, 5:1-3:1 elution) to give 3-{[2-(4,5-diphenyloxazol-2-yl)-2-cyclohexen-1-yl]methyl}-N-(phenethyl)benzenesulfonamide (54.3 mg, 22%).

Workup

  1. washwashed with 1N hydrochloric acid, water, saturated sodium hydrogencarbonate solution, water and brine
  2. dry with materialdried over magnesium sulfate
  3. customevaporated in vacuo
  4. customThe residue was purified by silica gel column chromatography (hexane:EtOAc, 5:1-3:1 elution)

Sources & evidence

ORD record
ord-4535e6c49ebb49a4a2d236cd72574483
Source dataset
uspto-grants-2002_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06437146B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes