Benzoyl chloride → HCID 21842644, compound

HRID 1737455Notes

Reaction equation

HRID 1737455 reaction equation
C(N(CC)C(C)C)(C)C.[CH3:10][NH:11][CH2:12][CH2:13][CH:14]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:15][CH2:16][OH:17].[C:24](Cl)(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>ClCCl>[OH:17][CH2:16][CH2:15][CH:14]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[CH2:13][CH2:12][N:11]([CH3:10])[C:24](=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 81531DiisopropylethylamineHCID 21842589HCID 21842589, compound

Product 1

HCID 21842644HCID 21842644, compoundYield 93.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

N,N-Diisopropylethylamine (0.352 mL, 261 mg, 2.02 mmol) and 5-(methylamino)-3-phenylpentan-1-ol (300 mg, 1.68 mmol) from Example 180, Step B, were dissolved in 4.0 mL of dichloromethane. The solution was cooled to 0° C., benzoyl chloride (0.205 mL, 248 mg, 1.77 mmol) was added dropwise, and the mixture was stirred for an additional 30 min. The mixture was then partitioned between 15 mL of dichloromethane and 15 mL of saturated aqueous sodium bicarbonate solution. The aqueous layer was extracted with 2×15 mL of dichloromethane. The combined organic extracts were washed with 20 mL of brine, dried over sodium sulfate, and evaporated. The crude product was purified by flash column chromatography on silica gel, eluting with 10% ethyl acetate in dichloromethane, to give 467 mg of the title compound. 1NMR (400 MHz, CD3OD) was complicated by the presence of a mixture of rotamers: δ 7.45-7.06 (m, 9H), 6.97 (d, 1H, J=8 Hz), 3.53-3.23 (m, 2H), 3.17-3.00 (m, 2H), 3.02 and 2.85 (two singlets, 3H), 2.88-2.78 and 2.57-2.49 (two multiplets, 1H), 2.07-1.64 (m, 4H). Mass spectrum (ESI): m/z=298 (M+1).

Workup

  1. customThe mixture was then partitioned between 15 mL of dichloromethane and 15 mL of saturated aqueous sodium bicarbonate solution
  2. extractionThe aqueous layer was extracted with 2×15 mL of dichloromethane
  3. washThe combined organic extracts were washed with 20 mL of brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customThe crude product was purified by flash column chromatography on silica gel
  7. washeluting with 10% ethyl acetate in dichloromethane

Sources & evidence

ORD record
ord-13fcaeb613b443f0a1590838dcab50ea
Source dataset
uspto-grants-1999_10
Patent number
US05962462

Reaction notes

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