Cyanogen Bromide → HCID 86656706, compound

HRID 451436Notes

Reaction equation

Cl.[CH2:2]([C:9]1[CH:14]=[C:13]([CH3:15])[N:12]=[C:11]([NH:16][CH:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)[N:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(=O)([O-])O.[Na+].[C:28](Br)#[N:29]>C(Cl)Cl.O>[CH2:2]([C:9]1[CH:14]=[C:13]([CH3:15])[N:12]=[C:11]([NH:16][CH:17]2[CH2:22][CH2:21][N:20]([C:28]#[N:29])[CH2:19][CH2:18]2)[N:10]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of (4-benzyl-6-methyl-pyrimidin-2-yl)-piperidin-4-yl-amine hydrochloride (255 mg, 0.8 mmol) in CH2Cl2 (1.5 mL) was added at 0° C. a suspension of sodium hydrogencarbonate (202 mg, 2.49 mmol) in water (0.5 mL) and then within 1 minute a solution of bromocyan (106 mg, 0.97 mmol) in CH2Cl2 (1 mL). The reaction was stirred at 0° C. for 45 minutes and then at room temperature over night. The reaction was diluted with CH2Cl2, washed with saturated aqueous NaHCO3 solution and with saturated aqueous NaCl solution, dried over sodium sulfate, filtered and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography using a gradient from CH2Cl2 to CH2Cl2/MeOH 19:1 (v/v) as eluent. The title compound was obtained as a colorless oil (135 mg, 55%).

Workup

waitat room temperature over night
washwashed with saturated aqueous NaHCO3 solution and with saturated aqueous NaCl solution
dry with materialdried over sodium sulfate
filtrationfiltered
customthe solvent was evaporated under reduced pressure
customThe residue was purified by column chromatography

Sources & evidence

ORD record: ord-ab132d7836484e4eb606e6248e0d396d
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08486967B2

Reaction notes

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