Acetyl chloride → HCID 68503208, compound

HRID 1176501Notes

Reaction equation

HRID 1176501 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[C:9]2[CH:10]=[C:11]([CH2:14][O:15][CH:16]3[CH:21]([C:22]4[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH2:30][CH2:31][O:32][C:33]5[CH:38]=[C:37]([F:39])[CH:36]=[CH:35][C:34]=5[F:40])=[CH:24][CH:23]=4)[CH2:20][CH2:19][N:18]([C:41]([O:43][CH2:44][C:45]4[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=4)=[O:42])[CH2:17]3)[CH:12]=[CH:13][C:8]=2[O:7][CH2:6][CH2:5]1.C(N(CC)CC)C.[C:58](Cl)(=[O:60])[CH3:59]>ClCCl>[C:58]([NH:1][CH2:2][CH2:3][N:4]1[C:9]2[CH:10]=[C:11]([CH2:14][O:15][CH:16]3[CH:21]([C:22]4[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH2:30][CH2:31][O:32][C:33]5[CH:38]=[C:37]([F:39])[CH:36]=[CH:35][C:34]=5[F:40])=[CH:24][CH:23]=4)[CH2:20][CH2:19][N:18]([C:41]([O:43][CH2:44][C:45]4[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=4)=[O:42])[CH2:17]3)[CH:12]=[CH:13][C:8]=2[O:7][CH2:6][CH2:5]1)(=[O:60])[CH3:59]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 68501850HCID 68501850, compound

Product 1

HCID 68503208HCID 68503208, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The solution of 0.220 g of benzyl 3-[4-(2-aminoethyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-4-{4-[3-(2,5-difluorophenoxy)propoxy]phenyl}piperidine-1-carboxylate in 7.5 ml of dichloromethane is cooled to 0° C. with stirring and admixed with 0.042 ml of triethylamine. 0.023 ml of acetyl chloride in 0.50 ml of dichloromethane are slowly added dropwise. Subsequently, the mixture is stirred at 0° C. over 1 hour. The reaction mixture is poured onto ice-water (20 ml) and extracted with tert-butyl methyl ether (2×20 ml). The organic phases are washed with brine (20 ml), dried over sodium sulphate and concentrated by evaporation. The title compound is obtained as a white foam from the residue by means of flash chromatography (SiO2 60F). Rf=0.75 (200:20:1 dichloromethane-methanol-25% conc. ammonia); Rt=5.46.

Workup

  1. stirringSubsequently, the mixture is stirred at 0° C. over 1 hour
  2. additionThe reaction mixture is poured onto ice-water (20 ml)
  3. extractionextracted with tert-butyl methyl ether (2×20 ml)
  4. washThe organic phases are washed with brine (20 ml)
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-dcd7909bafa14a2095cdaf8e8c4d0c15
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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