Sodium Iodide → tert-Butyl 4-(3-(1,1,1-trifluoro-2-methylpropan-2-ylcarbamoyl)benzyl)piperazine-1-carboxylate

HRID 1878417Notes

Reaction equation

HRID 1878417 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[C:5]([CH:16]=[CH:17][CH:18]=1)[C:6]([NH:8][C:9]([CH3:15])([CH3:14])[C:10]([F:13])([F:12])[F:11])=[O:7].[N:19]1([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1.[I-].[Na+].C(N(CC)CC)C>O.C(OCC)(=O)C>[F:11][C:10]([F:13])([F:12])[C:9]([NH:8][C:6]([C:5]1[CH:4]=[C:3]([CH:18]=[CH:17][CH:16]=1)[CH2:2][N:22]1[CH2:21][CH2:20][N:19]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:24][CH2:23]1)=[O:7])([CH3:15])[CH3:14]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 668783493-(chloromethyl)-N-(1,1,1-trifluoro-2-methylpropan-2-yl)benzamide

Product 1

HCID 86635136tert-Butyl 4-(3-(1,1,1-trifluoro-2-methylpropan-2-ylcarbamoyl)benzyl)piperazine-1-carboxylateYield 97.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-(Chloromethyl)-N-(1,1,1-trifluoro-2-methylpropan-2-yl)benzamide (3.10 mmol, 868 mg), tert-butyl piperazine-1-carboxylate (3.10 mmol, 578 mg), sodium iodide (3.10 mmol, 465 mg) and triethylamine (3.10 mmol, 0.433 mL) were all combined in actetonitrile (28 ml) and heated to reflux for 2 hours. After this time the reaction mixture was allowed to cool and ethyl acetate and water were added. The organic layer was separated, dried and concentrated under vacuum to yield the title compound (1.3 g).

Workup

  1. temperatureheated
  2. temperatureto reflux for 2 hours
  3. temperatureto cool
  4. customThe organic layer was separated
  5. customdried
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-890a1e933f444017af32c53d01b63d69
Source dataset
uspto-grants-2012_11
Patent number
US08314091B2

Reaction notes

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