Acetyl chloride → HCID 56597942, compound

HRID 1750154Notes

Reaction equation

HRID 1750154 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][CH2:18][O:19][C:20]2[CH:21]=[CH:22][C:23]([CH3:27])=[C:24]([CH:26]=2)[NH2:25])[CH2:11][CH2:10]1.[C:28](Cl)(=[O:30])[CH3:29].CCN(CC)CC>C(Cl)Cl.O>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N:9]1[CH2:10][CH2:11][N:12]([CH2:15][CH2:16][CH2:17][CH2:18][O:19][C:20]2[CH:21]=[CH:22][C:23]([CH3:27])=[C:24]([NH:25][C:28](=[O:30])[CH3:29])[CH:26]=2)[CH2:13][CH2:14]1

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 68628529HCID 68628529, compound

Product 1

HCID 56597942HCID 56597942, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of intermediate 63 (120 mg, 0.29 mmol), acetyl chloride (35 mg, 0.44 mmol) and Et3N (54 mg, 0.54 mmol) was dissolved in DCM and the solution was stirred at rt. The solution was diluted with water and extracted with DCM. The combined organic layers were washed with saturated aq NaHCO3, brine, dried over anhydrous Na2SO4, concentrated in vacuo and purified by flash chromatography on silica gel column (elution with DCM/MeOH=100:1-30:1) to give N-(5-(4-(4-(2,3-dichlorophenyl)piperazin-1-yl)butoxy)-2-methylphenyl)acetamide (compound 43) (45 mg, 35%) as a yellow solid. 1H NMR (300 MHz, CDCl3): δ 7.56 (s, 1H), 7.18-7.13 (m, 2H), 7.07-6.88 (m, 3H), 6.62 (d, J=8.1 Hz, 1H), 3.99 (br, 2H), 3.26 (br, 4H), 2.92-2.75 (br, 6H), 2.21 (s, 3H), 2.19 (s, 3H), 1.86 (br, 6H). HPLC: 99%, RT 2.464 min. MS (ESI) m/z 449.8 [M+H]+.

Workup

  1. extractionextracted with DCM
  2. washThe combined organic layers were washed with saturated aq NaHCO3, brine
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated in vacuo
  5. custompurified by flash chromatography on silica gel column (elution with DCM/MeOH=100:1-30:1)

Sources & evidence

ORD record
ord-ef6bc7f6bdb84f9895dc5dd3900725c4
Source dataset
uspto-grants-2015_10
Patent number
US09156822B2

Reaction notes

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