Water → HCID 19909372, compound

HRID 2073225Notes

Reaction equation

HRID 2073225 reaction equation
[NH2-].[Na+].[C:3]1([CH2:13][C:14]#[N:15])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1.[CH2:16]([CH:23]1[CH2:28][CH2:27][N:26]([CH2:29][CH2:30]Cl)[CH2:25][CH2:24]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O>CCOCC>[CH2:16]([CH:23]1[CH2:28][CH2:27][N:26]([CH2:29][CH2:30][CH:13]([C:3]2[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH:6]=[CH:5][CH:4]=2)[C:14]#[N:15])[CH2:25][CH2:24]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 85961-NaphthaleneacetonitrileHCID 24533Sodium amideHCID 15870313HCID 15870313, compound

Product 1

HCID 19909372HCID 19909372, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

2 g of sodium amide are added in small portions to a solution of naphth-1-ylacetonitrile in 150 ml of anhydrous ether and the mixture is refluxed for 5 hours. 11.8 g of 2-(4-benzylpiperidino)chloroethane are then added and the mixture is refluxed again for 3.5 hours. 200 ml of water are added and the organic phase is decanted and extracted with 300 ml of 10% hydrochloric acid. The aqueous phase is washed with ether, neutralized with 30% sodium hydroxide and extracted with ether. The organic phase is washed with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate and the solvent is then evaporated off to give 16.4 g of the expected product.

Workup

  1. temperaturethe mixture is refluxed for 5 hours
  2. temperaturethe mixture is refluxed again for 3.5 hours
  3. customthe organic phase is decanted
  4. extractionextracted with 300 ml of 10% hydrochloric acid
  5. washThe aqueous phase is washed with ether
  6. extractionextracted with ether
  7. washThe organic phase is washed with a saturated aqueous solution of sodium chloride
  8. dry with materialdried over magnesium sulfate
  9. customthe solvent is then evaporated off

Sources & evidence

ORD record
ord-6a39b645ea0d4457877fbe4e7111c2b6
Source dataset
uspto-grants-1990_04
Patent number
US04916156

Reaction notes

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