Acetic Acid → HCID 67445097, compound

HRID 1667105Notes

Reaction equation

HRID 1667105 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[C:5]([C:9](=O)[CH3:10])[CH:6]=[CH:7][CH:8]=1.[N:14]1([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.C(O)(=O)C.C([BH3-])#N.[Na+]>C(O)C>[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[C:5]([CH:9]([N:17]2[CH2:16][CH2:15][N:14]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:19][CH2:18]2)[CH3:10])[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 676823'-(Trifluoromethyl)acetophenoneHCID 143452tert-Butyl piperazine-1-carboxylateHCID 5003444Sodium cyanoborohydride

Product 1

HCID 67445097HCID 67445097, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

A suspension of 1-(3-(trifluoromethyl)phenyl)ethanone (0.100 g, 0.532 mmol), tert-butyl piperazine-1-carboxylate (0.148 g, 0.797 mmol), acetic acid (0.046 mL, 0.797 mmol) and sodium cyanoborohydride (0.050 g, 0.797 mmol) in ethanol (0.5 mL) was heated under nitrogen at 75° C. After stirring overnight the reaction was concentrated, saturated sodium bicarbonate (0.7 mL) was added, and the product was extracted into ethyl acetate (2×0.7 mL). The combined organic layers were concentrated, dissolved in a minimal amount of dichloromethane, loaded directly onto a SF15-12 silica gel column (Analogix®, Burlington, Wis.), and the title compound was eluted using a gradient of 2% to 20% ethyl acetate/hexanes over 20 minutes (flow=30 mL/minute).

Workup

  1. concentrationwas concentrated
  2. additionsaturated sodium bicarbonate (0.7 mL) was added
  3. extractionthe product was extracted into ethyl acetate (2×0.7 mL)
  4. concentrationThe combined organic layers were concentrated
  5. dissolutiondissolved in a minimal amount of dichloromethane
  6. washthe title compound was eluted
  7. customover 20 minutes

Sources & evidence

ORD record
ord-55d43212932b45bca2f1bc063c5f5a5a
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Reaction notes

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