Propylene Oxide → HCID 86759512, compound

HRID 1836417Notes

Reaction equation

HRID 1836417 reaction equation
Cl.[NH2:2][C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][CH:16]=1)[C:6]([CH:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=[O:7].C1OC1C.[F:21][C:22]1[CH:30]=[CH:29][C:25]([C:26]([Cl:28])=[O:27])=[CH:24][CH:23]=1>C(O)C>[ClH:28].[F:21][C:22]1[CH:30]=[CH:29][C:25]([C:26]([NH:2][C:3]2[CH:4]=[C:5]([CH:14]=[CH:15][CH:16]=2)[C:6]([CH:8]2[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]2)=[O:7])=[O:27])=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 6378Propylene OxideHCID 678794-Fluorobenzoyl chlorideHCID 69356056HCID 69356056, compound

Product 1

HCID 86759512HCID 86759512, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-(3-aminobenzoyl)piperidine HCl (10.87 g (45.15 mmol)) was suspended in absolute ethanol (220 mL) in presence of propylene oxide (3.185 g, 3.84 mL, 54.84 mmol) at room temperature for 15 min. p-fluorobenzoyl chloride (8.93 g, 6.65 mL, 56.44 mmol) was then added dropwise. During the addition, a partial dissolution was observed before the formation of a thick precipitate. The temperature rose from 22° C. to 33° C. during the acylation. The suspension was post-agitated at room temperature for 4 h. Then, the precipitate was filtered, washed with ethanol (22 mL) and diethylether (40 mL). 15.38 g (94%) of 4-[3-(4-fluorobenzamidyl)benzoyl]piperidine HCl were obtained after drying at 50° C. under vacuum for 12 hours.

Workup

  1. additionDuring the addition
  2. dissolutiona partial dissolution
  3. customrose from 22° C. to 33° C. during the acylation
  4. filtrationThen, the precipitate was filtered
  5. washwashed with ethanol (22 mL) and diethylether (40 mL)

Sources & evidence

ORD record
ord-f6c33699c80a48a88bbf8e38054417cc
Source dataset
uspto-grants-2004_08
Patent number
US06777428B1

Reaction notes

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