Hexane → Ethyl 4-benzyl-1-(5-bromopyrimidin-2-yl)piperidine-4-carboxylate

HRID 712218Notes

Reaction equation

HRID 712218 reaction equation
[CH2:1]([C:8]1([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[Br:28][C:29]1[CH:30]=[N:31][C:32](Cl)=[N:33][CH:34]=1.CCCCCC>CCO>[CH2:1]([C:8]1([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:9][CH2:10][N:11]([C:32]2[N:33]=[CH:34][C:29]([Br:28])=[CH:30][N:31]=2)[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 81531DiisopropylethylamineHCID 6066655-Bromo-2-chloropyrimidineHCID 53297794Ethyl 4-benzylpiperidine-4-carboxylate

Product 1

HCID 66977252Ethyl 4-benzyl-1-(5-bromopyrimidin-2-yl)piperidine-4-carboxylateYield 45%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 4-benzylpiperidine-4-carboxylate (0.46 g, 1.86 mmol) in EtOH (10.0 mL) was added DIPEA (0.80 mL, 4.65 mmol) at rt which was stirred at rt for 10 minutes followed by addition of 5-bromo-2-chloropyrimidine (0.30 g, 1.55 mmol). The reaction was heated up to 70° C. for 1 h. After completion of reaction (by TLC), solvent was evaporated and the crude residue purified over 100-200 M silica-gel using 4% EtOAc:hexane to obtain the desired product as a yellow solid (0.108 g, 45% yield). 1H NMR (DMSO-d6): δ 1.16 (t, J=7.20 Hz, 3H), 1.47 (m, 2H), 2.00 (m, 2H), 2.80 (s, 2H), 2.97 (m, 2H), 4.08 (q, J=7.20 Hz, 2H), 4.40 (m, 2H), 7.02 to 7.27 (m, 5H) and 8.43 (s, 2H).

Workup

  1. temperatureThe reaction was heated up to 70° C. for 1 h
  2. customAfter completion of reaction (by TLC), solvent
  3. customwas evaporated
  4. customthe crude residue purified over 100-200 M silica-gel

Sources & evidence

ORD record
ord-760ea3094dde44b7aa1953e619763f75
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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