Benzoyl chloride → HCID 11101390, compound

HRID 635383Notes

Reaction equation

HRID 635383 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:10]([O:17][C:18]1[CH:19]=[C:20]2[C:24](=[CH:25][CH:26]=1)[NH:23][CH:22]=[C:21]2[CH2:27][CH2:28][N:29]([CH3:31])[CH3:30])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C>CN(C)C1C=CN=CC=1.ClCCl>[CH2:10]([O:17][C:18]1[CH:19]=[C:20]2[C:24](=[CH:25][CH:26]=1)[N:23]([C:1]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:8])[CH:22]=[C:21]2[CH2:27][CH2:28][N:29]([CH3:30])[CH3:31])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 590221H-Indole-3-ethanamine, N,N'-dimethyl-5-(phenylmethoxy)-

Product 1

HCID 11101390HCID 11101390, compoundYield 48.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Benzoyl chloride (217 ml, 1.9 mmol) was added to a stirred solution of [2-(5-benzyloxy-1H-indol-3-yl)ethyl]dimethylamine (500 mg, 1.7 mmol), triethylamine (473 ml, 3.4 mmol) and 4-(dimethylamino)pyridine (20 mg, 0.2 mmol) in dry dichloromethane (5 ml) at 0° C. The reaction was allowed to warm slowly to ambient temperature, and stirred at this temperature overnight. The reaction was quenched with saturated aqueous sodium hydrogen carbonate. The aqueous was then extracted with dichloromethane (×3). The combined extracts were dried (Na2SO4), filtered and evaporated. The residue was purified by chromatography on silica gel, eluting with dichloromethane/methanol/aqueous ammonia (80:8:1) to give the title compound (327 mg, 48%) is a thick oil. δH (250 MHz, CDCl3) 2.30 (6H, s), 2.52-2.60 (2H, m), 2.78-2.84 (2H, m), 5.16 (2H, s), 7.06-7.10 (3H, m), 7.30-7.64 (10H, m), 8.28 (0.5H, s), 8.32 (0.5H, s).

Workup

  1. customThe reaction was quenched with saturated aqueous sodium hydrogen carbonate
  2. extractionThe aqueous was then extracted with dichloromethane (×3)
  3. dry with materialThe combined extracts were dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by chromatography on silica gel
  7. washeluting with dichloromethane/methanol/aqueous ammonia (80:8:1)

Sources & evidence

ORD record
ord-a9b4354fbc504b2d9ce2a45fec6eea27
Source dataset
uspto-grants-2001_02
Patent number
US06187805B1

Reaction notes

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