Triethylamine → HCID 19762454, compound

HRID 1613209Notes

Reaction equation

HRID 1613209 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)piperidine 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-4732d17c833e4a61a0915ab7c8da5845
Source dataset
uspto-grants-1993_03
Patent number
US05192776

Reaction notes

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