Tert-butyl 4-cyano-4-(cyclopropylmethyl)piperidine-1-carboxylate → 4-(Cyclopropylmethyl)piperidine-4-carbonitrile

HRID 551142Notes

Reaction equation

HRID 551142 reaction equation
[C:1]([C:3]1([CH2:16][CH:17]2[CH2:19][CH2:18]2)[CH2:8][CH2:7][N:6](C(OC(C)(C)C)=O)[CH2:5][CH2:4]1)#[N:2]>C(O)(C(F)(F)F)=O.C(Cl)Cl>[C:1]([C:3]1([CH2:16][CH:17]2[CH2:19][CH2:18]2)[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1)#[N:2]

Participants

4

Reactant 1

HCID 57425738Tert-butyl 4-cyano-4-(cyclopropylmethyl)piperidine-1-carboxylate

Product 1

HCID 594281874-(Cyclopropylmethyl)piperidine-4-carbonitrile

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of tert-butyl 4-cyano-4-cyclopropylmethylpiperidine-1-carboxylate (I-2) (1.00 g, 3.78 mmol) in TFA (50 mL) and DCM (75 mL) was stirred at room temperature for 0.5 h then the volatile components removed in vacuo. The residue was partitioned between saturated sodium bicarbonate solution and DCM. The organic phase was separated and the aqueous phase re-extracted with DCM twice. The combined organic phase was washed with brine, dried (MgSO4) and the solvent removed in vacuo to leave 4-cyano-4-cyclopropylmethylpiperidine (I-8) as a glass. 1H NMR (500 MHz, CD3OD): δ 3.03 (d, J=13.1 Hz, 2 H), 2.88-2.82 (m, 2 H), 2.00 (d, J=11.7 Hz, 2 H), 1.55-1.49 (m, 4 H), 0.92-0.84 (m, 1 H), 0.57-0.55 (m, 2 H), 0.20 (q, J=5.0 Hz, 2 H).

Workup

  1. customthe volatile components removed in vacuo
  2. customThe residue was partitioned between saturated sodium bicarbonate solution and DCM
  3. customThe organic phase was separated
  4. extractionthe aqueous phase re-extracted with DCM twice
  5. washThe combined organic phase was washed with brine
  6. dry with materialdried (MgSO4)
  7. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-179a23ad4bf844308f8dc17aa23a28eb
Source dataset
uspto-grants-2011_05
Patent number
US07947714B2

Reaction notes

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