Water → HCID 57436816, compound

HRID 46004Notes

Reaction equation

HRID 46004 reaction equation
C(N(CC)CC)C.[C:8](Cl)(=[O:10])[CH3:9].[CH2:12]([N:19]1[CH2:24][CH2:23][C:22]([CH2:37][NH2:38])([N:25]2[CH2:30][CH2:29][N:28]([C:31]3[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=3)[CH2:27][CH2:26]2)[CH2:21][CH2:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.O>ClCCl.[Cl-].[Na+].O>[CH2:12]([N:19]1[CH2:24][CH2:23][C:22]([CH2:37][NH:38][C:8](=[O:10])[CH3:9])([N:25]2[CH2:26][CH2:27][N:28]([C:31]3[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=3)[CH2:29][CH2:30]2)[CH2:21][CH2:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 57989584(1-Benzyl-4-(4-(pyridin-4-yl)piperazin-1-yl)piperidin-4-yl)methanamine

Product 1

HCID 57436816HCID 57436816, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

Triethylamine (2.5 equiv.) followed by acetyl chloride (1.2 equiv.) were added under cooled conditions to a solution of (1-benzyl-4-(4-(pyridin-4-yl)piperazin-1-yl)piperidin-4-yl)methanamine (4.67 mmol, 1 equiv.) in dichloromethane. The resulting solution was warmed to room temperature and stirred for 3 h. The mixture was diluted with dichloromethane and given water and brine washes respectively. The organic layer was dried over sodium sulfate, filtered and the solvent removed. The crude product was purified by column chromatography (silica). Yield: 52%

Workup

  1. dry with materialThe organic layer was dried over sodium sulfate
  2. filtrationfiltered
  3. customthe solvent removed
  4. customThe crude product was purified by column chromatography (silica)

Sources & evidence

ORD record
ord-026b9d6173864575a921b07de95d3d6c
Source dataset
uspto-grants-2013_09
Patent number
US08541573B2

Reaction notes

Loading…