Acetyl chloride → HCID 11996164, compound

HRID 2102683Notes

Reaction equation

HRID 2102683 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=3)([CH:12]3[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:33](Cl)(=[O:35])[CH3:34]>O1CCCC1>[C:33]([N:15]1[CH2:16][CH2:17][CH:12]([C:6]2([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=3)[C:5]3[C:9](=[CH:10][C:2]([Cl:1])=[CH:3][CH:4]=3)[NH:8][C:7]2=[O:11])[CH2:13][CH2:14]1)(=[O:35])[CH3:34]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 57803074HCID 57803074, compound

Product 1

HCID 11996164HCID 11996164, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of rac-6-chloro-3-(3-chloro-benzyl)-3-piperidin-4-yl-1,3-dihydro-indol-2-one (35 mg, 0.09 mmol) (from Example 15a supra) in tetrahydrofuran (3 mL) was added triethylamine (14.1 mg, 0.139 mmol), followed by the addition of acetyl chloride (8.7 mg, 0.11 mmol) (Aldrich). The mixture was stirred at room temperature for 30 minutes. The mixture was partitioned between ethyl acetate and water. The aqueous layer was extracted with another two portions of ethyl acetate. The combined organic layers were washed with water, brine, dried over Na2SO4 and concentrated to give rac-3-(1-acetyl-piperidin-4-yl)-6-chloro-3-(3-chloro-benzyl)-1,3-dihydro-indol-2-one as a white solid. (Yield 25 mg, 65%). Further purification by precipitation in a cosolvent of dichloromethane and hexanes gave the product as a white solid. (18 mg).

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. extractionThe aqueous layer was extracted with another two portions of ethyl acetate
  3. washThe combined organic layers were washed with water, brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-33d26595eb98437191c6f43519288e42
Source dataset
uspto-grants-2009_08
Patent number
US07576082B2

Reaction notes

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