Acetyl chloride → HCID 68497203, compound

HRID 1176352Notes

Reaction equation

HRID 1176352 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([CH2:13][O:14][CH:15]3[CH:20]([C:21]4[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH2:29][CH2:30][O:31][CH2:32][C:33]5[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=5[O:39][CH3:40])=[CH:23][CH:22]=4)[CH2:19][CH2:18][N:17]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH2:16]3)[CH:11]=2)[C:6]([CH3:49])([CH3:48])[CH2:5]1.[C:50](Cl)(=[O:52])[CH3:51]>C(N(CC)CC)C.ClCCl>[C:50]([NH:1][CH2:2][CH2:3][N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([CH2:13][O:14][CH:15]3[CH:20]([C:21]4[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH2:29][CH2:30][O:31][CH2:32][C:33]5[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=5[O:39][CH3:40])=[CH:23][CH:22]=4)[CH2:19][CH2:18][N:17]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH2:16]3)[CH:11]=2)[C:6]([CH3:49])([CH3:48])[CH2:5]1)(=[O:52])[CH3:51]

Participants

5

Reactant 2

HCID 6367Acetyl chlorideHCID 68501535HCID 68501535, compound

Product 1

HCID 68497203HCID 68497203, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

The solution of 0.268 g of tert-butyl 3-[1-(2-aminoethyl)-3,3-dimethyl-2,3-dihydro-1H-indol-6-ylmethoxy]-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate in 0.061 ml of triethylamine and 9.0 ml of dichloromethane is cooled to 0° C. and admixed slowly with the solution of 0.033 ml of acetyl chloride in 1.0 ml of dichloromethane. The reaction solution is stirred over a further 30 minutes, poured onto ice-water (20 ml) and extracted with tert-butyl methyl ether (2×20 ml). The organic phases are washed successively with water (20 ml) and brine (20 ml), dried over sodium sulphate, filtered and concentrated by evaporation. The title compound is obtained as a yellowish oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.73 (200:20:1 dichloromethane-methanol-conc. ammonia); Rt=5.82.

Workup

  1. additionpoured onto ice-water (20 ml)
  2. extractionextracted with tert-butyl methyl ether (2×20 ml)
  3. washThe organic phases are washed successively with water (20 ml) and brine (20 ml)
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-1443219295f642dba602622829e306c1
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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