Hydrochloric Acid → (2R*,4S*)-2-Benzyl-N-(4-quinolylmethyl)-N-trifluoroacetyl-4-piperidinamine

HRID 264611Notes

Reaction equation

HRID 264611 reaction equation
Cl.[CH2:2]([C@@H:9]1[CH2:14][C@@H:13]([N:15]([CH2:22][C:23]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[N:26]=[CH:25][CH:24]=2)[C:16](=[O:21])[C:17]([F:20])([F:19])[F:18])[CH2:12][CH2:11][N:10]1C(OC(C)(C)C)=O)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>O1CCOCC1>[CH2:2]([C@@H:9]1[CH2:14][C@@H:13]([N:15]([CH2:22][C:23]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[N:26]=[CH:25][CH:24]=2)[C:16](=[O:21])[C:17]([F:19])([F:20])[F:18])[CH2:12][CH2:11][NH:10]1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57080478(2R*,4S*)-2-Benzyl-1-t-butyloxycarbonyl-N-(4-quinolylmethyl)-N-trifluoroacetyl-4-piperidinamine

Product 1

HCID 57202094(2R*,4S*)-2-Benzyl-N-(4-quinolylmethyl)-N-trifluoroacetyl-4-piperidinamine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

250 ml of 6N hydrogen chloride in dioxane is added dropwise over the course of 3 minutes to 7.73 g (14.7 mmol) of (2R*,4S*)-2-benzyl-1-t-butyloxycarbonyl-N-(4-quinolylmethyl)-N-trifluoroacetyl-4-piperidinamine while cooling in ice, and the mixture is subsequently stirred at room temperature for 1 hour. The reaction mixture is concentrated in a rotary evaporator, basified with 1N sodium bicarbonate solution and extracted with methylene chloride. The organic phases are dried over magnesium sulfate and evaporated to dryness. The brownish oil (7.14 g) is chromatographed on silica gel with methylene chloride/methanol/conc. ammonia (700:50:1). The title compound is obtained as yellow oil. TLC: methylene chloride/methanol/conc. ammonia (700:50:1) Rf =0.42, DCI-MS: (M+H)+ =428, IR: 1690 cm-1.

Workup

  1. temperaturewhile cooling in ice
  2. concentrationThe reaction mixture is concentrated in a rotary evaporator
  3. extractionextracted with methylene chloride
  4. dry with materialThe organic phases are dried over magnesium sulfate
  5. customevaporated to dryness
  6. customThe brownish oil (7.14 g) is chromatographed on silica gel with methylene chloride/methanol/conc

Sources & evidence

ORD record
ord-8e468c60108c4e59a886aa52b72926a8
Source dataset
uspto-grants-1997_07
Patent number
US05646144

Reaction notes

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