Triethylamine → N-phenoxycarbonyl-(R)-2-(2, 3-methylenedioxyphenyl) heptylamine

HRID 1756784Notes

Reaction equation

HRID 1756784 reaction equation
[CH2:1]1[O:9][C:8]2[C:3](=[C:4]([C@@H:10]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:11][NH2:12])[CH:5]=[CH:6][CH:7]=2)[O:2]1.C(N(CC)CC)C.Cl[C:26]([O:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:27]>C(OCC)(=O)C>[O:28]([C:26]([NH:12][CH2:11][C@@H:10]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[O:9][CH2:1][O:2][C:3]=12)[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[O:27])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 10331642(R)-2-(2, 3-methylenedioxyphenyl) heptylamine

Product 1

HCID 54262691N-phenoxycarbonyl-(R)-2-(2, 3-methylenedioxyphenyl) heptylamineYield 98.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 2.35 g of (R)-2-(2, 3-methylenedioxyphenyl) heptylamine, 1.20 g of triethylamine and 20 ml of ethyl acetate was dropwise added 1.72 g of phenyl chloroformate with ice cooling and stirring, and the resultant mixture was stirred at room temperature for 2 hours. The reaction mixture was washed with water and saturated saline in this order, dried over anhydrous sodium sulfate and the solvent evaporated to give 3.51 g of N-phenoxycarbonyl-(R)-2-(2, 3-methylenedioxyphenyl) heptylamine.

Workup

  1. washThe reaction mixture was washed with water and saturated saline in this order
  2. dry with materialdried over anhydrous sodium sulfate
  3. customthe solvent evaporated

Sources & evidence

ORD record
ord-01d1182842f141eaa9bc45a31711cee7
Source dataset
uspto-grants-1995_08
Patent number
US05442060

Reaction notes

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