Benzylamine → HCID 19895565, compound

HRID 892455Notes

Reaction equation

HRID 892455 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:30]2[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=2)=[CH:9][CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][C:15]([C:28]#[CH:29])([O:18][C:19]([O:21]C3C=CC=CC=3)=O)[CH2:14][CH2:13]2)=[CH:4][CH:3]=1.[CH2:37]([NH2:44])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>C1C=CC=CC=1>[CH2:37]([NH:44][C:19]([O:18][C:15]1([C:28]#[CH:29])[CH2:14][CH2:13][N:12]([CH2:11][CH2:10][CH:9]=[C:8]([C:30]2[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=2)[C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[CH2:17][CH2:16]1)=[O:21])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 19895582HCID 19895582, compound

Product 1

HCID 19895565HCID 19895565, compoundYield 75.7%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

9.8 g of 1-[4,4-bis(4-fluorophenyl)-3-butenyl]-4-ethynyl -4-phenoxycarbonyloxypiperidine are stirred with 9 ml of benzylamine at 42° C. under nitrogen for 30 minutes, then at room temperature for 10 hours. Thereafter, benzene is added to the reaction mixture and washed first with an aqueous sodium hydroxide solution of 1 ml/liter concentration, then with water and dried over anhydrous magnesium sulfate. After evaporating the solution under reduced pressure, the residue is boiled in hexane and after filtration it is recrystallization from diisopropyl ether to give the title product in 75.7% yield, m.p.: 94°-95° C.

Workup

  1. washwashed first with an aqueous sodium hydroxide solution of 1 ml/liter concentration
  2. dry with materialwith water and dried over anhydrous magnesium sulfate
  3. customAfter evaporating the solution under reduced pressure
  4. filtrationafter filtration it
  5. customrecrystallization from diisopropyl ether

Sources & evidence

ORD record
ord-6d385072e86e434da6d6432c0f3b03ad
Source dataset
uspto-grants-1992_06
Patent number
US05118693

Reaction notes

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