4-Cyanopiperidine → Methyl 1-[(4-cyanopiperidin-1-yl)carbonyl]-5-[4-(trifluoromethyl)phenyl]piperidine-3-carboxylate

HRID 876261Notes

Reaction equation

HRID 876261 reaction equation
[F:1][C:2]([F:32])([F:31])[C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][N:13]([C:15]([O:17]C3C=CC([N+]([O-])=O)=CC=3)=O)[CH2:12][CH:11]([C:27]([O:29][CH3:30])=[O:28])[CH2:10]2)=[CH:5][CH:4]=1.[NH:33]1[CH2:38][CH2:37][CH:36]([C:39]#[N:40])[CH2:35][CH2:34]1>>[C:39]([CH:36]1[CH2:37][CH2:38][N:33]([C:15]([N:13]2[CH2:14][CH:9]([C:6]3[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:31])[F:32])=[CH:8][CH:7]=3)[CH2:10][CH:11]([C:27]([O:29][CH3:30])=[O:28])[CH2:12]2)=[O:17])[CH2:34][CH2:35]1)#[N:40]

Participants

3

Reactant 2

HCID 1382234-CyanopiperidineHCID 580023253-Methyl 1-(4-nitrophenyl) 5-[4-(trifluoromethyl)phenyl]piperidine-1,3-dicarboxylate

Product 1

HCID 58002422Methyl 1-[(4-cyanopiperidin-1-yl)carbonyl]-5-[4-(trifluoromethyl)phenyl]piperidine-3-carboxylate

Procedure

4.00 g (8.84 mmol) of 3-methyl 1-(4-nitrophenyl) 5-[4-(trifluoromethyl)phenyl]piperidine-1,3-dicarboxylate (Example 58A) and 2.92 g (26.5 mmol) of piperidine-4-carbonitrile were reacted according to the General Method 8A. Yield: 3.15 g (77% of theory)

Sources & evidence

ORD record
ord-2e1d1304f29c4b9faa11eb41a881f363
Source dataset
uspto-grants-2015_03
Patent number
US08987248B2

Reaction notes

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