Dipropylamine → HCID 9920908, compound

HRID 1840763Notes

Reaction equation

HRID 1840763 reaction equation
[CH:1]([C:3]1[CH2:8][CH2:7][CH2:6][C:5](=[O:9])[CH:4]=1)=[CH2:2].[CH2:10]([NH:13][CH2:14][CH2:15][CH3:16])[CH2:11][CH3:12].C([O-])([O-])=O.[Cs+].[Cs+].[K+].[Br-]>C(#N)C.C(OCC)C>[CH2:10]([N:13]([CH2:14][CH2:15][CH3:16])[CH2:2][CH2:1][C:3]1[CH2:8][CH2:7][CH2:6][C:5](=[O:9])[CH:4]=1)[CH2:11][CH3:12]

Participants

7

Reactant 4

HCID 8902DipropylamineHCID 10796Cesium carbonateHCID 253877Potassium BromideHCID 117685623-Vinyl-cyclohex-2-enone

Product 1

HCID 9920908HCID 9920908, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

3-Vinyl-cyclohex-2-enone (0.75 g, 6.1 mmol) (prepared according to Nasarow's method) was dissolved in acetonitril (1 mL) and dipropylamine (1.5 g, 16 mmol) was added followed by Cs2CO3 (50 mg). After stirring the mixture at rt for 3 h it was diluted with diethylether (100 mL), filtered and evaporated to dryness. The residue was destilled in vacuo (175° C., 0.01 mm Hg) to give a slightly yellow oil which was converted to the hydrochloride salt. Recrystallization from isopropyl ether/isopropyl alcohol yielded: 1.2 g, 4.6 mmol (75%), mp 95-97° C. IR (KBr) 2962, 2613, 1667; 1H-NMR (CDCl3) δ5.84 (d, 1H), 2.65 (m, 2H), 2.27-2.60 (m, 9H), 1.99 (m, 2H), 1.39-1.51 (m, 5H), 0.86 (t, 6H) ppm; 13C-NMR (CDCl3) δ198.2, 163.5, 124.9, 54.2, 50.1, 35.7, 33.7, 28.4, 21.2, 18.5, 10.4 ppm; MS (EI) m/z 223 (M+).

Workup

  1. filtrationfiltered
  2. customevaporated to dryness
  3. customwas destilled in vacuo (175° C., 0.01 mm Hg)
  4. customto give a slightly yellow oil which
  5. customRecrystallization from isopropyl ether/isopropyl alcohol
  6. customyielded

Sources & evidence

ORD record
ord-edf82cc1ea694067a6da3953dbc12038
Source dataset
uspto-grants-2004_01
Patent number
US06683087B2

Reaction notes

Loading…