Triethylamine → HCID 19762454, compound

HRID 248863Notes

Reaction equation

HRID 248863 reaction equation
Cl.[F:2][C:3]1[C:15]([F:16])=[C:14]([F:17])[C:13]([F:18])=[C:12]([F:19])[C:4]=1[O:5][CH:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1.C(N(CC)CC)C.[CH3:27][N:28]=[C:29]=[O:30]>C1C=CC=CC=1>[CH3:27][NH:28][C:29]([N:9]1[CH2:10][CH2:11][CH:6]([O:5][C:4]2[C:12]([F:19])=[C:13]([F:18])[C:14]([F:17])=[C:15]([F:16])[C:3]=2[F:2])[CH2:7][CH2:8]1)=[O:30]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12228Methyl IsocyanateHCID 19762467HCID 19762467, compound

Product 1

HCID 19762454HCID 19762454, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a stirring solution of 5.3 g of 4-(2,3,4,5,6-pentafluorophenoxy)piperdine hydrochloride in 100 ml of benzene was added 2.37 ml of triethylamine followed by 1.00 ml of methyl isocyanate. The reaction mixture was stirred at ambient temperature for three hours and then evaporated to a semi-solid. The semi-solid was purified by means of high pressure liquid chromatography (silica gel; elution with 50% ethyl acetate/dichloromethane) to afford 5.14 g (93.3%) of 1-[(N-methylamino)carbonyl]-4-(2,3,4,5,6-pentafluorophenoxy)piperidine, m.p. 107°-110° C.

Workup

  1. customevaporated to a semi-solid
  2. customThe semi-solid was purified by means of high pressure liquid chromatography (silica gel; elution with 50% ethyl acetate/dichloromethane)

Sources & evidence

ORD record
ord-eb6fde2a0c4c4131859e84797d8db214
Source dataset
uspto-grants-1993_05
Patent number
US05212184

Reaction notes

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