Diisopropylethylamine → HCID 11500190, compound

HRID 915993Notes

Reaction equation

HRID 915993 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[CH2:9][NH2:10].C(N(C(C)C)CC)(C)C.[C:20]1([CH:26]([CH2:30][CH3:31])[C:27](Cl)=[O:28])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[CH2:9][NH:10][C:27](=[O:28])[CH:26]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:30][CH3:31]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 981732-Phenylbutyryl chlorideHCID 177507992-Fluoro-5-methylbenzenemethanamine

Product 1

HCID 11500190HCID 11500190, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (2-fluoro-5-methylphenyl)methanamine (1-f, 50 mg, 0.26 mmol, Oakwood Products, Inc., West Columbia, S.C.) and diisopropylethylamine (88 uL, 0.52 mmol) in dichloromethane (1 mL) was treated at room temperature with 2-phenylbutanoyl chloride (1-a, 47 mg, 0.26 mmol). The reaction mixture was stirred for 30 min, partitioned between dichloromethane and 0.1N—NaOH. The aqueous layer was removed and the organic layer was washed with 0.1N—HCl. The aqueous layer was removed by filtering through a plastic frit. The organic layer was evaporated in vacuo to give the desired product (1-2); HRMS (M+1)=286.1586.

Workup

  1. custompartitioned between dichloromethane and 0.1N—NaOH
  2. customThe aqueous layer was removed
  3. washthe organic layer was washed with 0.1N—HCl
  4. customThe aqueous layer was removed
  5. filtrationby filtering through a plastic frit
  6. customThe organic layer was evaporated in vacuo

Sources & evidence

ORD record
ord-81fa414fc51d4498a41a08a69ea1d50c
Source dataset
uspto-grants-2007_09
Patent number
US07268153B2

Reaction notes

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