Triethylamine → HCID 57325230, compound

HRID 264626Notes

Reaction equation

HRID 264626 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].C(N(CC)CC)C.[CH2:19]([C@@H:26]1[CH2:31][C@@H:30]([N:32]([CH2:39][C:40]2[C:49]3[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=3)[N:43]=[CH:42][CH:41]=2)[C:33](=[O:38])[C:34]([F:37])([F:36])[F:35])[CH2:29][CH2:28][NH:27]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(Cl)Cl>[CH2:19]([C@@H:26]1[CH2:31][C@@H:30]([N:32]([CH2:39][C:40]2[C:49]3[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=3)[N:43]=[CH:42][CH:41]=2)[C:33](=[O:38])[C:34]([F:36])([F:37])[F:35])[CH2:29][CH2:28][N:27]1[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 10387Benzyl chloroformate2×HCID 57202094(2R*,4S*)-2-Benzyl-N-(4-quinolylmethyl)-N-trifluoroacetyl-4-piperidinamine

Product 1

HCID 57325230HCID 57325230, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

67 μl (0.468 mmol) of benzyl chloroformate and 72 μl (0.515 mol) of triethylamine are added to a solution of 200 mg (0.468 mmol) of (2R*,4S*)-2-benzyl-N-(4-quinolylmethyl)-N-trifluoroacetyl-4-piperidinamine in 4 ml methylene chloride at 0°, and the mixture is left to stir at this temperature for 16 hours. Then a further 34 μl (0.234 mmol) of benzyl chloroformate and 36 μl (0.257 mmol) of triethylamine are added and stirred at room temperature for 3 hours. This is followed by dilution with methylene chloride, and the organic phase is washed with brine, dried over magnesium sulfate and evaporated to dryness. The oil is chromatographed on silica gel with methylene chloride/methanol/conc. ammonia (1000:50:1). The title compound is obtained as oil. TLC: methylene chloride/methanol/conc. ammonia (700:50:1) Rf =0.61, FD-MS: M+ =561.

Workup

  1. waitthe mixture is left
  2. stirringstirred at room temperature for 3 hours
  3. washthe organic phase is washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated to dryness
  6. customThe oil is chromatographed on silica gel with methylene chloride/methanol/conc

Sources & evidence

ORD record
ord-ee01694bfa724c8388e0043e5bc022b2
Source dataset
uspto-grants-1997_07
Patent number
US05646144

Reaction notes

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