Hydrochloric Acid → HCID 20343959, compound

HRID 2049864Notes

Reaction equation

HRID 2049864 reaction equation
[H-].[Na+].[C:3]1([S:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH2:16][C:17]#[N:18])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:19][N:20]([CH2:24][CH2:25]Cl)[CH2:21][CH2:22][Cl:23].Cl.Cl>CN(C)C=O.CCOCC>[ClH:23].[C:17]([C:16]1([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[S:9][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:25][CH2:24][N:20]([CH3:19])[CH2:21][CH2:22]1)#[N:18]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 5935Nitrogen mustard hydrochlorideHCID 24758Sodium hydrideHCID 123285452-(Phenylthio)benzeneacetonitrile

Product 1

HCID 20343959HCID 20343959, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent3×HCID 6228DimethylformamideSolvent2×

Procedure

2.6 g of 99% sodium hydride are added portionwise to a solution of 4.4 g of 2-(phenylthio)phenylacetonitrile in 50 ml of dimethylformamide. The resulting reddish brown mixture is stirred for 30 minutes before adding dropwise a solution of 4.0 g of mechlorethamine hydrochloride in 50 ml of dimethylformamide, maintaining gas evolution at a slow rate. After total addition, the mixture is stirred at 80°-85° C. for 15 hours. Thereafter, 100 g of ice are added before the mixture is extracted thrice with ether. The combined ether extracts are dried over potassium carbonate and then the solvent is removed under vacuum leaving a brownish oil. The oil is dissolved in a small amount of ether and passed through, with additional ether, an alumina column which is packed in ether. The effluent is concentrated leaving an oil which is converted to its hydrochloride which is recrystallized from an acetone-ether mixture, leaving 4-cyano-1-methyl-4-(2-phenylthiophenyl)piperidine hydrochloride.

Workup

  1. temperaturemaintaining gas evolution at a slow rate
  2. additionAfter total addition
  3. stirringthe mixture is stirred at 80°-85° C. for 15 hours
  4. extractionis extracted thrice with ether
  5. dry with materialThe combined ether extracts are dried over potassium carbonate
  6. customthe solvent is removed under vacuum
  7. customleaving a brownish oil
  8. concentrationThe effluent is concentrated
  9. customleaving an oil which
  10. customis recrystallized from an acetone-ether mixture

Sources & evidence

ORD record
ord-d9faa95ae7334c51a3448028224a7fcf
Source dataset
uspto-grants-1980_04
Patent number
US04198419

Reaction notes

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