Hydrochloric Acid → HCID 11773119, compound

HRID 1984983Notes

Reaction equation

HRID 1984983 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:20]=[CH:19][C:18](F)=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(Cl)(Cl)Cl.[Cl:26][CH:27]([CH2:30][CH3:31])[C:28]#N.[Cl-].[Cl-].[Cl-].[Al+3].Cl.C(=O)([O-])[O-:38].[Na+].[Na+]>C1C=CC=CC=1.C(Cl)Cl.O>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[C:28](=[O:38])[CH:27]([Cl:26])[CH2:30][CH3:31])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 25135Boron TrichlorideHCID 1002042-ChlorobutyronitrileHCID 5109634Despropionyl N-benzyl p-fluoro norfentanylHCID 6451240Aluminum(III) Chloride

Product 1

HCID 11773119HCID 11773119, compound

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

(1-Benzyl-piperidine-4-yl)-(4-fluoro-phenyl)-amine (51.2 g) is dissolved in 180 ml benzene and cooled down with an ice bath. Borontrichloride (180 ml, 1 M hexane solution) is added drop wise over 30 min. 2-Chlorbutyronitrile (18.6 g) and aluminiumtrichloride (24.0 g) are added and the resulting mixture is heated under reflux for 15 h. Then the mixture is cooled down, 180 ml of 2N HCl, are added and the mixture is further refluxed. 200 ml Water and 200 ml CH2Cl2 are added and the resulting mixture adjusted to pH=5 with portions of sodium carbonate. The phases are separated, the organic phase is dried with sodium sulphate and the solvent is removed. The resulting oil is purified with flash column chromatography (96:4 CH2Cl2:MeOH). Yield is 20.7 g of a colourless oil.

Workup

  1. temperaturecooled down with an ice bath
  2. temperaturethe resulting mixture is heated
  3. temperatureunder reflux for 15 h
  4. temperatureThen the mixture is cooled down
  5. customThe phases are separated
  6. dry with materialthe organic phase is dried with sodium sulphate
  7. customthe solvent is removed
  8. customThe resulting oil is purified with flash column chromatography (96:4 CH2Cl2:MeOH)

Sources & evidence

ORD record
ord-be2e6a1bd1454d3698ba1e59624e1119
Source dataset
uspto-grants-2009_06
Patent number
US07544806B2

Reaction notes

Loading…