Dipropylamine → HCID 9920908, compound

HRID 890594Notes

Reaction equation

HRID 890594 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 destined 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) δ 5.84 (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) δ 198.2, 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 destined 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-e2dc39d8fc224662a95d45e75eea0282
Source dataset
uspto-grants-2006_02
Patent number
US06998405B2

Reaction notes

Loading…