Acetyl chloride → HCID 22038030, compound

HRID 1790410Notes

Reaction equation

HRID 1790410 reaction equation
[NH2:1][CH2:2][C:3]1[CH:25]=[CH:24][C:6]([CH2:7][CH2:8][N:9]2[CH2:14][CH2:13][CH:12]([N:15]3[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH2:17][CH2:16]3)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.[C:26](Cl)(=[O:28])[CH3:27].C(=O)(O)[O-].[Na+]>O1CCCC1>[C:26]([NH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][CH2:8][N:9]2[CH2:14][CH2:13][CH:12]([N:15]3[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH2:17][CH2:16]3)[CH2:11][CH2:10]2)=[CH:24][CH:25]=1)(=[O:28])[CH3:27]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 220382211-[1-(4-Aminomethylphenethyl)piperidin-4-yl]indoline

Product 1

HCID 22038030HCID 22038030, compoundYield 79.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-[1-(4-Aminomethylphenethyl)piperidin-4-yl]indoline (0.6 g) was dissolved in tetrahydrofuran (9.0 ml). Under ice cooling, acetyl chloride (0.14 ml) was added dropwise thereinto and the resultant mixture was stirred for 2 hr. After adding a saturated aqueous solution of sodium bicarbonate, the mixture was extracted with ethyl acetate, washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by Cromatorex NH silica gel column chromatography (hexane/ethyl acetate system) to give the title compound (0.518 g) as a pale yellow oil (yield: 79.2%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by Cromatorex NH silica gel column chromatography (hexane/ethyl acetate system)

Sources & evidence

ORD record
ord-c4d8ab43de154be5b60ed348ae175194
Source dataset
uspto-grants-2006_07
Patent number
US07071201B2

Reaction notes

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