Sodium Hydroxide → [1-(3-Chloropropyl)piperidin-4-yl](4-fluorophenyl)methanone

HRID 2397443Notes

Reaction equation

HRID 2397443 reaction equation
S(Cl)([Cl:3])=O.[F:5][C:6]1[CH:23]=[CH:22][C:9]([C:10]([CH:12]2[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][CH2:20]O)[CH2:14][CH2:13]2)=[O:11])=[CH:8][CH:7]=1.[OH-].[Na+]>C(Cl)(Cl)Cl>[F:5][C:6]1[CH:23]=[CH:22][C:9]([C:10]([CH:12]2[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][CH2:20][Cl:3])[CH2:14][CH2:13]2)=[O:11])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 124044224-(p-Fluorobenzoyl)-1-(3-hydroxypropyl)piperidine

Product 1

HCID 12404419[1-(3-Chloropropyl)piperidin-4-yl](4-fluorophenyl)methanoneYield 92%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Thionyl chloride (38.7 g., 0.376 mole) was added dropwise to a stirring solution of 4-(p-fluorobenzoyl)-1-(3-hydroxypropyl) piperidine (43.1 g., 0.163 mole) in 400 ml. chloroform at room temperature. After the addition was complete the reaction mixture was stirred at room temperature an additional 16 hours. The mixture was then chilled and 125 ml. 6N sodium hydroxide solution was added dropwise. The chloroform solution was separated, washed with water, and dried over magnesium sulfate. Removal of the solvent gave 42.7 g. crude product (92% yield) with crystallized on cooling. Recrystallization from isooctane gave 25.3 g. pure product, m.p. 66.5°-68.5° C.

Workup

  1. customat room temperature
  2. additionAfter the addition
  3. temperatureThe mixture was then chilled
  4. customThe chloroform solution was separated
  5. washwashed with water
  6. dry with materialdried over magnesium sulfate
  7. customRemoval of the solvent
  8. customgave 42.7 g

Sources & evidence

ORD record
ord-eaf6fbe3e16345a8851111ee591ee237
Source dataset
uspto-grants-1977_05
Patent number
US04021552

Reaction notes

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