Water → HCID 13039273, compound

HRID 1106348Notes

Reaction equation

HRID 1106348 reaction equation
[F:1][C:2]1[CH:20]=[CH:19][C:5]([O:6][C@@H:7]2[CH2:12][CH2:11][NH:10][CH2:9][C@H:8]2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH:28]1([C:31](Cl)=[O:32])[CH2:30][CH2:29]1.O>C(Cl)(Cl)Cl.CCCCCC>[CH:28]1([C:31]([N:10]2[CH2:11][CH2:12][C@@H:7]([O:6][C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:20][CH:19]=3)[C@H:8]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:9]2)=[O:32])[CH2:30][CH2:29]1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 77637Cyclopropanecarbonyl chlorideHCID 12788502HCID 12788502, compound

Product 1

HCID 13039273HCID 13039273, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 8058HexaneSolvent

Procedure

To a mixture of 5.42 g of trans-4-(4-fluorophenoxy)-3-phenylpiperidine, 3.06 ml of triethylamine and 150 ml of chloroform is added, dropwise at room temperature under nitrogen, a solution of 2.0 ml of cyclopropylcarbonyl chloride in 100 ml of chloroform over a 20 minute period. A cold water bath is used to keep the temperature below 30° C. during the addition. After 105 minutes the reaction mixture is treated with 150 ml of water. After several minutes of vigorous stirring, the phases are separated and the chloroform phase is washed with 2 N hydrochloric acid (100 ml), saturated sodium chloride solution (150 ml), dried overnight over anhydrous sodium sulfate, filtered and concentrated in vacuo to afford a yellow oil which solidifies upon trituration with hexane. Recrystallization from 75 ml of boiling cyclohexane affords product as nearly colorless crystals, mp 113°-115° C.

Workup

  1. additionis added, dropwise at room temperature under nitrogen
  2. customA cold water bath is used
  3. customthe temperature below 30° C.
  4. additionduring the addition
  5. waitAfter several minutes of vigorous stirring
  6. customthe phases are separated
  7. washthe chloroform phase is washed with 2 N hydrochloric acid (100 ml), saturated sodium chloride solution (150 ml)
  8. dry with materialdried overnight over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customto afford a yellow oil which
  12. customRecrystallization from 75 ml of boiling cyclohexane
  13. customaffords product as nearly colorless crystals, mp 113°-115° C.

Sources & evidence

ORD record
ord-5a33536837664858ad34e97e06b44ba1
Source dataset
uspto-grants-1982_01
Patent number
US04312876

Reaction notes

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