Hydrochloric Acid → HCID 12915170, compound

HRID 2081821Notes

Reaction equation

HRID 2081821 reaction equation
[ClH:1].[CH:2]1([CH2:8][NH:9][CH:10]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N+:18]([O-])=O)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.C(O)C.[OH-].[K+].Cl>CCOCC>[ClH:1].[ClH:1].[NH2:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[CH2:11][CH:10]([NH:9][CH2:8][CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14797Potassium HydroxideHCID 12915162HCID 12915162, compound

Product 1

HCID 12915170HCID 12915170, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

7.0 g of N-Cyclohexylmethyl-2-nitro-α-phenylphenethylamine hydrochloride is treated with 200 ml of warm 95% ethanol containing 2.07 of potassium hydroxide for 15 minutes, after which the mixture is filtered and placed in a Paar flask containing 0.35 g of 10% palladium on charcoal. The mixture is hydrogenated at 50 psia for 2 hours. After removal of the catalyst, the ethanol is evaporated and the resulting biphasic mixture is poured onto 200 ml of water. The aqueous mixture is extracted with methylene chloride (2×200 ml). The combined methylene chloride extracts are dried over anhydrous magnesium sulfate and the methylene chloride is evaporated giving a colorless oil. The oil is dissolved in 100 ml of ether. Ethereal hydrogen chloride (200 ml) is a added and the salt precipitates from solution. The hydrochloride salt is collected as a gummy powder, which is recrystallized from i-propanol to provide crystals, mp 205° C. dec, 2-amino-N-cyclohexylmethyl-α-phenylphenethylamine dihydrochloride.

Workup

  1. filtrationafter which the mixture is filtered
  2. additioncontaining 0.35 g of 10% palladium on charcoal
  3. customAfter removal of the catalyst
  4. customthe ethanol is evaporated
  5. additionthe resulting biphasic mixture is poured onto 200 ml of water
  6. extractionThe aqueous mixture is extracted with methylene chloride (2×200 ml)
  7. dry with materialThe combined methylene chloride extracts are dried over anhydrous magnesium sulfate
  8. customthe methylene chloride is evaporated
  9. customgiving a colorless oil
  10. additiona added
  11. customthe salt precipitates from solution
  12. customThe hydrochloride salt is collected as a gummy powder, which
  13. customis recrystallized from i-propanol

Sources & evidence

ORD record
ord-e6f92af015a04e6ca50ac347c16f5663
Source dataset
uspto-grants-1993_02
Patent number
US05185465

Reaction notes

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