Acetyl chloride → HCID 178473768, compound

HRID 635314Notes

Reaction equation

HRID 635314 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][C:17]3[NH:18][N:19]=[C:20]4[CH2:25][CH2:24][NH:23][CH2:22][C:21]=34)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[C:26](Cl)(=[O:28])[CH3:27]>C(Cl)(Cl)Cl.C(=O)([O-])O.[Na+]>[C:26]([N:23]1[CH2:24][CH2:25][C:20]2=[N:19][NH:18][C:17]([CH2:16][CH2:15][CH2:14][N:11]3[CH2:10][CH2:9][N:8]([C:5]4[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=4)[CH2:13][CH2:12]3)=[C:21]2[CH2:22]1)(=[O:28])[CH3:27]

Participants

5

Reactant 2

HCID 6367Acetyl chlorideHCID 178505854HCID 178505854, compound

Product 1

HCID 178473768HCID 178473768, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 516892Sodium BicarbonateSolvent

Procedure

3-(3-(4-(4-Fluorophenyl)piperazin-1-yl)propyl)-4,5,6,7-tetrahydro-2H-pyrazolo[4,3-c]pyridine (0.3 g) obtained in Example 141 was dissolved in a mixed solution of chloroform (5 ml) and saturated aqueous sodium hydrogencarbonate solution (5 ml), and acetyl chloride (0.3 ml) was added dropwise under ice-cooling. After the dropwise addition, the chloroform layer was partitioned and dried over magnesium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was subjected to silica gel column chromatography to give 5-acetyl-3-(3-(4-(4-fluorophenyl)piperazin-1-yl)propyl)-4,5,6,7-tetrahydro-2H-pyrazolo[4,3-c]pyridine.

Workup

  1. additionwas added dropwise under ice-
  2. temperaturecooling
  3. additionAfter the dropwise addition
  4. customthe chloroform layer was partitioned
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-770c040aaf0b4628b514775a867d998b
Source dataset
uspto-grants-2001_02
Patent number
US06187774B1

Reaction notes

Loading…