3-Bromopropionitrile → tert-Butyl 1-(2-cyanoethyl)piperidin-4-ylcarbamate

HRID 2239550Notes

Reaction equation

HRID 2239550 reaction equation
Br[CH2:2][CH2:3][C:4]#[N:5].[NH:6]1[CH2:11][CH2:10][CH:9]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:8][CH2:7]1>CC#N>[C:4]([CH2:3][CH2:2][N:6]1[CH2:7][CH2:8][CH:9]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:16])([CH3:18])[CH3:17])[CH2:10][CH2:11]1)#[N:5]

Participants

4

Reactant 2

HCID 170203-BromopropionitrileHCID 7238334-(N-Boc-amino)piperidine

Product 1

HCID 59862765tert-Butyl 1-(2-cyanoethyl)piperidin-4-ylcarbamateYield 32%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

3-Bromopropionitril (0.74 g, 5.49 mmol) was added to a solution of tert-butyl piperidin-4-ylcarbamate (1.00 g, 4.99 mmol) and TEA (0.56 g, 5.49 mmol) in MeCN (15 mL), and the mixture was heated at 60° C. for 5 h and then evaporated. The residue was purified by silica gel column chromatography (Horizons Biotage) using a 40:60 and then 15:85-10:90 mixture of heptane and EtOAc as eluant, to give the title compound (0.40 g, 32%). 1H NMR (500 MHz, CDCl3): δ 4.44 (br s, 1H), 3.54-3.42 (br m, 1H), 2.88-2.79 (m 2H), 2.69 (t, 2H), 2.51 (t 2H), 2.24-2.16 (m, 2H), 1.99-1.92 (m 2H), 1.47 (s 9H), 1.49-1.41 (m 2H); 13C NMR (125 MHz, CDCl3): δ 155.4, 119.0, 53.6, 52.2, 47.7, 32.7, 28.6, 16.4.

Workup

  1. customevaporated
  2. customThe residue was purified by silica gel column chromatography (Horizons Biotage)
  3. addition15:85-10:90 mixture of heptane and EtOAc as eluant

Sources & evidence

ORD record
ord-e8fd8a3c198747479fb4743f39701656
Source dataset
uspto-grants-2010_05
Patent number
US07723333B2

Reaction notes

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