Cyclohexene → 2-((3-amino-2-cyanophenoxy)methyl)-N-ethylpiperidine-1-carboxamide

HRID 332976Notes

Reaction equation

[C:1]([C:3]1[C:21]([N+:22]([O-])=O)=[CH:20][CH:19]=[CH:18][C:4]=1[O:5][CH2:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][N:8]1[C:13]([NH:15][CH2:16][CH3:17])=[O:14])#[N:2].C1CCCCC=1>CCO.[Pd]>[NH2:22][C:21]1[C:3]([C:1]#[N:2])=[C:4]([CH:18]=[CH:19][CH:20]=1)[O:5][CH2:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][N:8]1[C:13]([NH:15][CH2:16][CH3:17])=[O:14]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 2-((2-cyano-3-nitrophenoxy)methyl)-N-ethylpiperidine-1-carboxamide (Example 26c, 0.458 g, 1.46 mmol) in EtOH (20 mL) was added cyclohexene (0.74 mL, 7.3 mmol) and catalytic amount of 10% Pd/C (0.146 mg). Reaction mixture was heated at 100° C. for 40 minutes, then filtered through Cellite, washed with EtOH (100 mL) and evaporated to give 2-((3-amino-2-cyanophenoxy)methyl)-N-ethylpiperidine-1-carboxamide (0.407 g, 92%) which was used in to next step without further purification. MS 303 (MH+).

Workup

customReaction mixture
filtrationfiltered through Cellite
washwashed with EtOH (100 mL)
customevaporated

Sources & evidence

ORD record: ord-956c315dce5845a2b537f15c2b7b5dda
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08877922B2

Reaction notes

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