Acetyl chloride → HCID 178513916, compound

HRID 72847Notes

Reaction equation

HRID 72847 reaction equation
[F:1][C:2]1[CH:25]=[CH:24][C:5]2[C:6]([CH:9]3[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH:17]4[CH2:22][CH2:21][CH:20](N)[CH2:19][CH2:18]4)[CH2:11][CH2:10]3)=[N:7][O:8][C:4]=2[CH:3]=1.[CH2:26]([N:28](CC)CC)[CH3:27].C(Cl)(=[O:35])C.C(=O)(O)[O-].[Na+]>ClCCl>[F:1][C:2]1[CH:25]=[CH:24][C:5]2[C:6]([CH:9]3[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][C@H:17]4[CH2:18][CH2:19][C@H:20]([CH2:27][C:26]([NH2:28])=[O:35])[CH2:21][CH2:22]4)[CH2:11][CH2:10]3)=[N:7][O:8][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 252062094-{2-[4-(6-Fluoro-benzo[d]isoxazol-3-yl)-piperidin-1-yl]-ethyl}-cyclohexylamine

Product 1

HCID 178513916HCID 178513916, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-{2-[4-(6-Fluoro-benzo[d]isoxazol-3-yl)-piperidin-1-yl]-ethyl}-cyclohexylamine (0.03 g, 0.087 mmol) is suspended in dichloromethane (0.600 mL) and triethylamine is added (0.013 mL, 0.096 mmol) followed by acetylchloride (0.008 mL, 0.104 mmol) and the mixture was stirred for 30 minutes at room temperature until TLC indicated the end of the reaction. Sodium bicarbonate solution was added until pH 9 and the reaction extracted 3 times with dichloromethane. The organic phase was dried and purified with column chromatography on silica gel using CH2Cl2—CH2Cl2/MeOH (1-9:1). The product fractions were concentrated to give 0.022 g (0.056 mmol, 65% yield) of a white solid. MS (m/e): 388.5 (M+H+).

Workup

  1. customthe end of the reaction
  2. extractionthe reaction extracted 3 times with dichloromethane
  3. customThe organic phase was dried
  4. custompurified with column chromatography on silica gel
  5. concentrationThe product fractions were concentrated

Sources & evidence

ORD record
ord-422d5652f87e425c853773d4821fa564
Source dataset
uspto-grants-2014_09
Patent number
US08829029B2

Reaction notes

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