Iodine → HCID 57589953, compound

HRID 1924964Notes

Reaction equation

HRID 1924964 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]([N:5]1[CH2:10][CH2:9][CH:8]([C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=2)[CH2:7][CH2:6]1)=O.N#N.[BH4-].[Na+].II>C1COCC1>[F:21][C:2]([F:1])([F:20])[CH2:3][N:5]1[CH2:6][CH2:7][CH:8]([C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=2)[CH2:9][CH2:10]1

Participants

6

Reactant 4

HCID 807IodineHCID 947NitrogenHCID 4311764Sodium borohydrideHCID 542857602,2,2-Trifluoro-1-[4-(4-nitrophenyl)piperidin-1-yl]ethan-1-one

Product 1

HCID 57589953HCID 57589953, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 1-trifluoroacetyl-4-(4-nitrophenyl)piperidine (1.42 g, 4.7 mmol) in THF (15 mL) is stirred in 25 mL 2-necked flask fitted with a condenser and pressure-equalising addition funnel. The system is flushed with N2, NaBH4 (210 mg, 5.6 mmol) is added and the flask is cooled to 0° C. A solution of iodine (600 mg, 2.3 mmol) in THF (5 mL) is then added dropwise over 20 minutes, after which the addition funnel is removed and the mixture heated at reflux overnight. The resulting pale yellow suspension is cooled to rt and MeOH (1.5 mL) is added cautiously, causing vigorous evolution of a gas. Evaporation of the solvents affords the title compound, which is used without further purification.

Workup

  1. customfitted with a condenser and pressure-equalising addition funnel
  2. additionis added
  3. customafter which the addition funnel is removed
  4. temperaturethe mixture heated
  5. temperatureat reflux overnight
  6. temperatureThe resulting pale yellow suspension is cooled to rt
  7. additionMeOH (1.5 mL) is added cautiously
  8. customEvaporation of the solvents

Sources & evidence

ORD record
ord-b841f190513548e482fc693f6ede6e3c
Source dataset
uspto-grants-2012_05
Patent number
US08178530B2

Reaction notes

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