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

HRID 712224Notes

Reaction equation

HRID 712224 reaction equation
Cl.[CH2:2]([C:5]1([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1)[CH:3]=[CH2:4].CCN(C(C)C)C(C)C.[Br:25][C:26]1[CH:27]=[N:28][C:29](Cl)=[N:30][CH:31]=1.CCCCCC>CCO>[CH2:2]([C:5]1([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:10][CH2:9][N:8]([C:29]2[N:30]=[CH:31][C:26]([Br:25])=[CH:27][N:28]=2)[CH2:7][CH2:6]1)[CH:3]=[CH2:4]

Participants

6

Reactant 4

HCID 8058HexaneHCID 81531DiisopropylethylamineHCID 6066655-Bromo-2-chloropyrimidineHCID 53429630Ethyl 4-allyl-4-piperidinecarboxylate hydrochloride

Product 1

HCID 66976988Ethyl 4-allyl-1-(5-bromopyrimidin-2-yl)piperidine-4-carboxylateYield 56%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 4-allylpiperidine-4-carboxylate hydrochloride (1.30 g, 6.59 mmol) in EtOH (20.0 mL) was added DIPEA (3.0 mL, 16.47 mmol) and the mixture stirred at rt for 10 min followed by addition of 5-bromo-2-chloropyrimidine (1.06 g, 5.49 mmol). The reaction was then heated up to 70° C. for 1 h. After reaction completion (by TLC), solvent was evaporated and the crude residue purified over 100-200 M silica-gel using 2.0% EtOAc:hexane to obtain the desired product as a yellow solid (1.0 g, 56% yield). 1H NMR (DMSO-d6): δ 1.19 (t, J=6.80 Hz, 3H), 1.44 (m, 2H), 2.02 (m, 2H), 2.27 (m, 2H), 3.10 (m, 2H), 4.13 (q, J=6.80 Hz, 2H), 4.29 (m, 2H), 5.06 (m, 2H), 5.66 (m, 1H) and 8.43 (s, 2H)

Workup

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

Sources & evidence

ORD record
ord-cb2c0794d3814577af878b3346b1011c
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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