Trifluoroacetic acid → 4-(Cyclopropylmethoxy)piperidine

HRID 1986824Notes

Reaction equation

HRID 1986824 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([O:14][CH2:15][CH:16]2[CH2:18][CH2:17]2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH:16]1([CH2:15][O:14][CH:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)[CH2:17][CH2:18]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 689110854-Cyclopropylmethoxypiperidine-1-carboxylic acid t-butyl ester

Product 1

HCID 171780104-(Cyclopropylmethoxy)piperidineYield 95.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A reaction flask was charged with 4-cyclopropylmethoxypiperidine-1-carboxylic acid t-butyl ester (6.80 g, 26.6 mmol) in DCM (15 mL). TFA (7 mL) was added and the reaction was stirred at rt for 4 h. The reaction mixture was quenched with 1 M NaOH and the product extracted into diethyl ether. The combined organic phases were dried over Na2SO4, filtered, and concentrated to give the title compound (3.949 g, 95%). 1H NMR (CD3CD) d 3.34-3.24 (m, 1H), 3.15 (d, 2H), 2.88-2.82 (m, 2H), 2.44-2.37 (m, 2H), 1.78-1.70 (m, 2H), 1.31-1.21 (m, 2H), 0.89-0.79 (m, 1H), 0.37-0.32 (m, 2H), 0.04-0.00 (m, 2H); 13C NMR (CD3OD) d 76.2, 73.6, 44.7, 33.2, 11.7, 3.5.

Workup

  1. customThe reaction mixture was quenched with 1 M NaOH
  2. extractionthe product extracted into diethyl ether
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-54b7cf330e5443e5a90c25e4d7765af1
Source dataset
uspto-grants-2009_06
Patent number
US07550459B2

Reaction notes

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