Triethylamine → 1-(2,6-Dimethylpyrimidin-4-yl)-4-(ethoxycarbonyl)piperidine

HRID 2289540Notes

Reaction equation

HRID 2289540 reaction equation
[CH3:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([CH3:9])[N:3]=1.[NH:10]1[CH2:20][CH2:19][CH:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:12][CH2:11]1.C(N(CC)CC)C>C(O)C>[CH3:1][C:2]1[N:7]=[C:6]([N:10]2[CH2:20][CH2:19][CH:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:12][CH2:11]2)[CH:5]=[C:4]([CH3:9])[N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 70770Ethyl 4-piperidinecarboxylateHCID 31541994-Chloro-2,6-dimethylpyrimidine

Product 1

HCID 186980321-(2,6-Dimethylpyrimidin-4-yl)-4-(ethoxycarbonyl)piperidineYield 92.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

2,6-Dimethyl-4-chloro-pyrimidine (1.0 g) in ethanol (10 ml) was added slowly to a solution of ethyl isonipecotate (1.1 g) and triethylamine (2.0 ml) in ethanol (20 ml). The reaction was stirred at room temperature overnight. The solvent was removed in vacuo and the residue was partitioned between ethyl acetate and water, washed with water (2×50 ml), dried and evaporated to give 1-(2,6-dimethylpyrimidin-4-yl)-4-(ethoxycarbonyl)piperidine as an oil (1.71 g); NMR (CDCl3): 1.25 (t, 3H), 1.65-1.80 (m, 4H), 1.95-2.00 (m, 2H), 2.55 (s, 3H), 2.45 (s, 3H), 2.50-2.60 (m, 1H), 3.00 (dt, 2H), 4.15 (q, 2H), 4.35 (d, 2H), 6.2 (s, 1H).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was partitioned between ethyl acetate and water
  3. washwashed with water (2×50 ml)
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-8511c32afedf4a8d9e3cabf7e171d583
Source dataset
uspto-grants-2000_07
Patent number
US06093718

Reaction notes

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