Hydrochloric Acid → HCID 178420402, compound

HRID 483605Notes

Reaction equation

HRID 483605 reaction equation
[C:1]([C:3]1[CH:32]=[CH:31][C:6]([O:7][CH2:8][CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][CH:14]([O:17][CH:18]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:13][CH2:12]2)=[CH:5][CH:4]=1)#[N:2].[Cl-].[NH4+].[N-:35]=[N+:36]=[N-:37].[Na+].Cl.N([O-])=O.[Na+]>CN(C)C=O.O.CCCCCC>[NH:35]1[C:1]([C:3]2[CH:4]=[CH:5][C:6]([O:7][CH2:8][CH2:9][CH2:10][N:11]3[CH2:16][CH2:15][CH:14]([O:17][CH:18]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH2:13][CH2:12]3)=[CH:31][CH:32]=2)=[N:2][N:37]=[N:36]1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 19753207HCID 19753207, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 178420402HCID 178420402, compoundYield 65.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Conditions

Temperature
45 °C

Procedure

1.67 g (3.92 mmol) of 1-[3-(4-cyanophenoxy)propyl]-4diphenylmethoxypiperidine dissolved in 15 ml of dimethylformamide was added 1.26 g (23.6 mmol) of ammonium chloride, and the mixture was stirred at 45° C. for 15 minutes. Subsequently, 1.02 g (15.7 mmol) of sodium azide was added to the mixture, and the mixture was stirred at 100° C. to 110° C. for 12 hours. After completion of the reaction, the reaction mixture was allowed to cool to 70° C., and a solution of 1.6 ml of conc. hydrochloric acid diluted with 50 ml of water was added. After the mixture was allowed to cool to 35° C., 10 ml of n-hexane and 1.35 g (19.6 mmol) of sodium nitrite in 5 ml of water were added to the mixture to give vigorous gas evolution and then an amber viscous product was liberated. After the supernatant was removed by decantation, 50 ml of ethyl acetate was added to the residual amber viscous product, and the mixture was shaken vigorously. The precipitated crystals were filteref off and washed sufficiently with ethyl acetate to obtain 1.20 g (yield: 65%) of 1-{3-[4-(1,2,3,4-tetrazol-5-yl)phenoxy]propyl)-4-diphenylmethoxypiperidine as pale brown crystals.

Workup

  1. stirringthe mixture was stirred at 100° C. to 110° C. for 12 hours
  2. customAfter completion of the reaction
  3. temperatureto cool to 70° C.
  4. additionwas added
  5. temperatureto cool to 35° C.
  6. customto give vigorous gas evolution
  7. customAfter the supernatant was removed by decantation, 50 ml of ethyl acetate
  8. additionwas added to the residual amber viscous product
  9. stirringthe mixture was shaken vigorously
  10. washwashed sufficiently with ethyl acetate

Sources & evidence

ORD record
ord-01df66d32ecd42a0bf0c35ed4e7f6e39
Source dataset
uspto-grants-1993_07
Patent number
US05225559

Reaction notes

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