Ethyl Bromide → HCID 61829791, compound

HRID 1725972Notes

Reaction equation

HRID 1725972 reaction equation
[CH2:1]1[CH2:6][CH2:5][N:4]([C:7]([CH2:9][C:10]#[N:11])=[O:8])[CH2:3][CH2:2]1.Br[CH2:13][CH3:14].[CH2:15]([Li])[CH2:16]CC.CCCCCC>C1COCC1>[CH2:15]([C:9]([C:7]([N:4]1[CH2:5][CH2:6][CH2:1][CH2:2][CH2:3]1)=[O:8])([CH2:13][CH3:14])[C:10]#[N:11])[CH3:16]

Participants

6

Reactant 4

HCID 6332Ethyl BromideHCID 8058HexaneHCID 847651-(Cyanoacetyl)piperidineHCID 178418339Butyllithium

Product 1

HCID 61829791HCID 61829791, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The compound was synthesized from 1-cyanoacetylpiperidine (1.52 g, 10 mmol), bromoethane (3.73 mL, 50 mmol) and 1.6M n-butyllithium in hexane (13.75 mL, 22 mmol) in 40 mL of THF according to the method described in Example 393A to give 0.92 g. MS (ESI(+)) m/e 209 (M+H)+; 226 (M+NH4)+; 1H NMR (300 MHz, DMSO-d6) δ 3.44-3.67 (m, 4H), 2.00-2.10 (m, 2H), 1.79-1.86 (m, 2H), 1.43-1.70 (m, 6H), 1.03-1.07 (m, 6H).

Workup

  1. customto give 0.92 g

Sources & evidence

ORD record
ord-72af481dfe344fc5bd3f633944dbf226
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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