Triethylamine → (R)-1-{4-[4-(3-Chloro-benzylidene)-piperidin-1-yl]-pyrimidin-2-yl}-ethyl butyrate

HRID 394527Notes

Reaction equation

HRID 394527 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([CH:13]=[CH:14][CH:15]=1)[CH:6]=[C:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1.[CH2:16](N(CC)CC)[CH3:17].[C:23]([O:26][C@@H:27]([C:29]1[N:34]=[C:33](Cl)[CH:32]=[CH:31][N:30]=1)[CH3:28])(=[O:25])[CH3:24]>ClCCl>[C:23]([O:26][C@@H:27]([C:29]1[N:34]=[C:33]([N:10]2[CH2:11][CH2:12][C:7](=[CH:6][C:5]3[CH:13]=[CH:14][CH:15]=[C:3]([Cl:2])[CH:4]=3)[CH2:8][CH2:9]2)[CH:32]=[CH:31][N:30]=1)[CH3:28])(=[O:25])[CH2:24][CH2:16][CH3:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 223286604-(3-Chlorobenzylidene)-piperidine hydrochlorideHCID 54154993(R)-1-(4-chloropyrimidin-2-yl)-ethyl acetate

Product 1

HCID 53807001(R)-1-{4-[4-(3-Chloro-benzylidene)-piperidin-1-yl]-pyrimidin-2-yl}-ethyl butyrate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(3-chlorobenzylidene)-piperidine hydrochloride (prepared according to the method of Example 176, Step B, 0.46 g, 2.0 mmol) and triethylamine (0.61 g, 6.0 mmol) in dichloromethane (10 mL) was added (R)-1-(4-chloropyrimidin-2-yl)-ethyl acetate (prepared according to the method of Preparation Five, 0.54 g, 2.2 mmol) and stirred at ambient temperature for 12 h. The mixture was washed successively with saturated aqueous sodium bicarbonate and water, and the organic layer was dried over sodium sulfate and filtered. The filtrate was concentrated to obtain a crude product which was purified by flash chromatography (95:5 dichloromethane:methanol) to give the title compound of Example 176, Step C as a viscous oil, 0.64 g (80%). 1H NMR (CDCl3, 300 MHz) δ 0.95 (d, 6H), 1.51 (d, 3H), 1.68 (m, 2H) 2.35 (m, 2H), 2.47-2.64 (m, 4H), 3.67-3.75 (m, 4H), 5.68 (q, 1H), 6.36 (s, 1H), 6.40 (d, 1H), 6.98 (m, 1H), 7.12-7.28 (m, 3H), 8.18 (m, 1H); MS (CI) 400 (MH+).

Workup

  1. customprepared
  2. customaccording to the method of Preparation Five, 0.54 g, 2.2 mmol) and
  3. washThe mixture was washed successively with saturated aqueous sodium bicarbonate and water
  4. dry with materialthe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. customto obtain a crude product which
  8. customwas purified by flash chromatography (95:5 dichloromethane:methanol)

Sources & evidence

ORD record
ord-2a69e18c641c4255828b59f0710dcd0b
Source dataset
uspto-grants-2003_08
Patent number
US06602875B2

Reaction notes

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