Phenethylamine → HCID 21255668, compound

HRID 636756Notes

Reaction equation

HRID 636756 reaction equation
[CH2:1]([NH2:9])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.N1C=CC=CC=1.[CH3:16][O:17][C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20](Cl)=[O:21]>ClCCl>[CH3:16][O:17][C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20](=[O:21])[CH2:8][CH2:7][CH2:6][C:5]1[CH:4]=[CH:3][CH:2]=[CH:1][N:9]=1

Participants

5

Reactant 3

HCID 1001PhenethylamineHCID 1049PyridineHCID 889692-Methoxybenzoyl chloride

Product 1

HCID 21255668HCID 21255668, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.5 gm of phenethylamine (4.12 mmol) in 5 mL of dichloromethane and 0.978 mL of pyridine (8.2 mmol) at 0° C. was added 1.39 gm of 2-methoxybenzoyl chloride (1.14 mL, 8.2 mmol). The reaction was allowed to warm to room temperature and was stirred for 4 hr. The reaction mixture was concentrated, 5mL of heptane were added and the mixture was evaporated to dryness this being repeated one more time. The residue was purified by HPLC (RCM SepPak, silica 25×100, 3.6% CH3CN, 14.4% tBuOCH3, 82% hexane) to give the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. addition5mL of heptane were added
  3. customthe mixture was evaporated to dryness
  4. customThe residue was purified by HPLC (RCM SepPak, silica 25×100, 3.6% CH3CN, 14.4% tBuOCH3, 82% hexane)

Sources & evidence

ORD record
ord-fbba823b36694015be887a6c2efd6543
Source dataset
uspto-grants-2001_02
Patent number
US06194458B1

Reaction notes

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