Sodium Iodide → HCID 23465843, compound

HRID 443803Notes

Reaction equation

HRID 443803 reaction equation
[C:1]1([CH:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[O:8][CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+].Cl[CH2:30][CH2:31][CH2:32][C:33]#[N:34]>CC(C)CC(=O)C>[C:33]([CH2:32][CH2:31][CH2:30][N:12]1[CH2:13][CH2:14][CH:9]([O:8][CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:10][CH2:11]1)#[N:34]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 123364-ChlorobutyronitrileHCID 30175844-Benzhydryloxypiperidine

Product 1

HCID 23465843HCID 23465843, compound

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

The starting material for said product No. (4) is prepared as follows. The mixture of 4.63 g of 4-diphenylmethoxypiperidine, 4.63 g of anhydrous sodium carbonate, 0.3 g of sodium iodide, 1.81 g of 4-chlorobutyronitrile and 60 ml of 4-methyl-2-pentanone is stirred and refluxed for 22 hours. It is evaporated, the residue taken up in diethyl ether, the solution washed with 2N aqueous sodium hydroxide and saturated aqueous sodium chloride, dried and evaporated, to give the 1-(3-cyanopropyl)-4-diphenylmethoxypiperidine, which is sufficiently pure to be used directly for the reduction to the 1-(4-aminobutyl)-4-diphenylmethoxypiperidine previously described.

Workup

  1. temperaturerefluxed for 22 hours
  2. customIt is evaporated
  3. washthe solution washed with 2N aqueous sodium hydroxide and saturated aqueous sodium chloride
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-4433e2cfc4ec414f8b48f798bffd399e
Source dataset
uspto-grants-1981_04
Patent number
US04261990

Reaction notes

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