Water → HCID 19043489, compound

HRID 1683328Notes

Reaction equation

HRID 1683328 reaction equation
[C:1](Cl)(=[O:4])[CH2:2][CH3:3].[CH3:6][CH:7]([CH3:17])[CH2:8][N:9]1[CH2:14][CH2:13][C:12]([CH3:16])([CH3:15])[CH:11]=[CH:10]1.C(N(CC)CC)C.O>ClCCl.C(OCC)C.CCCCCC>[CH3:6][CH:7]([CH3:17])[CH2:8][N:9]1[CH2:14][CH2:13][C:12]([CH3:15])([CH3:16])[C:11]([C:1](=[O:4])[CH2:2][CH3:3])=[CH:10]1

Participants

8

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 14955099HCID 14955099, compound

Product 1

HCID 19043489HCID 19043489, compoundYield 81%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolvent2×HCID 6344DichloromethaneSolvent2×HCID 8058HexaneSolvent

Procedure

Propionyl chloride (9.25 g, 0.1 mol) was added dropwise to a solution of 1-(2-methylpropyl)-4,4-dimethyl-1,4,5,6-tetrahydropyridine (16.7 g, 0.1 mol) and triethylamine (12.1 g, 0.12 mol) in dichloromethane (100 ml) stirring under an atmosphere of nitrogen at ice bath temperature. After one hour at this temperature, water (50 ml) was added, the organic layer was separated, washed with 5% aqueous sodium carbonate and dried over anhydrous MgSO4. Removal of the organic solvent afforded a yellow oil (22.3 g, quantitative) which was essentially pure by 90 MHz NMR spectroscopy. After column chromatography on silica-gel (Merck Kieselgel 60, 70-230 mesh) using 5% diethyl ether in dichloromethane (or 3:7 ether: n-hexane) as eluent, the pure 1-(2-methylpropyl)-3-propionyl-4,4-dimethyl-1,4,5,6-tetrahydropyridine (18.0 g, 81%) was obtained as a very pale yellow oil. UV λ max MeOH 307 nm, 29,300. 1H NMR (CDCl3) δ7.13 (1H, s), 3.10 (2H, m, AAIXXI system), 2.94 (2H, d, J7.4Hz), 2.44 (2H, q, J7.5Hz), 1.95 (1H, m, J6.6Hz, J7.4Hz), 1.60 (2H, m, AAIXXI system), 1.27 (6H, s), 1.08 (3H, t, J7.5 Jz), and 0.90 (6H, d, J6.6Hz). 13C NMR (CDCl3) δ195.9 (s), 147.9 (d), 114,4 (s), 64.1 (t), 43.3 (t), 39.3 (t), 30.0 (s), 29.7 (t), 28.1 (q), 27.4 (d), 19.8 (q), and 10.3 (q). MS 223.1913 (M+), 25.2%, 194 (100%).

Workup

  1. customthe organic layer was separated
  2. washwashed with 5% aqueous sodium carbonate
  3. dry with materialdried over anhydrous MgSO4
  4. customRemoval of the organic solvent
  5. customafforded a yellow oil (22.3 g, quantitative) which

Sources & evidence

ORD record
ord-44c776a8ca4b4be2a166e955bae14189
Source dataset
uspto-grants-1997_06
Patent number
US05637718

Reaction notes

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