1,3-Benzodioxole-5-carbonyl chloride → HCID 10225668, compound

HRID 1793241Notes

Reaction equation

HRID 1793241 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10](Cl)=[O:11])=[CH:9][C:4]=2[O:3][CH2:2]1.[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH2:23][CH2:24][NH:25][CH2:26][C@@H:27]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH3:28])[CH:18]=[CH:19][C:20]=1[O:21][CH3:22]>C(N(CC)CC)C>[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH2:23][CH2:24][N:25]([CH2:26][C@@H:27]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH3:28])[C:10]([C:8]2[CH:7]=[CH:6][C:5]3[O:1][CH2:2][O:3][C:4]=3[CH:9]=2)=[O:11])[CH:18]=[CH:19][C:20]=1[O:21][CH3:22]

Participants

4

Reactant 2

HCID 27347491,3-Benzodioxole-5-carbonyl chlorideHCID 11335556(2R)-N-[2-(3,4-Dimethoxyphenyl)ethyl]-2-phenylpropan-1-amine

Product 1

HCID 10225668HCID 10225668, compoundYield 74.5%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A stirring solution of benzo[1,3]dioxole-5-carbonyl chloride (151 mg, 0.82 mmol) in MDC (5 ml) was treated with a pre-mixed solution of (R)-[2-(3,4-dimethoxy-phenyl)-ethyl]-(2-phenyl-propyl)-amine (D12, 245 mg, 0.75 mmol) and triethylamine (0.17 ml) in MDC (2 ml). After stirring under argon at room temperature for 72 h the solvent was removed in vacuo and the residue was chromatographed (silica gel, 0–40% EtOAc-pentane) to afford the title compound as a colourless gum (250 mg, 68%).

Workup

  1. customwas removed in vacuo
  2. customthe residue was chromatographed (silica gel, 0–40% EtOAc-pentane)

Sources & evidence

ORD record
ord-1b6c9c55b1b4432a92c1ab271f086e9c
Source dataset
uspto-grants-2006_07
Patent number
US07078565B2

Reaction notes

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