Methanol → HCID 23658955, compound

HRID 426090Notes

Reaction equation

[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]([NH2:9])=[O:8])[CH2:3][CH2:2]1.[C:10]1([CH:16]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:17]2[CH2:20][C:19](=O)[CH2:18]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.CO>C(O)(=O)C>[C:10]1([CH:16]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:17]2[CH2:20][CH:19]([N:1]3[CH2:6][CH2:5][CH:4]([C:7]([NH2:9])=[O:8])[CH2:3][CH2:2]3)[CH2:18]2)[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To a mixture of piperidine-4-carboxamide (1.05 g, 8.2 mmol), 1-(diphenylmethyl)azetidin-3-one (see Bioorg. Med. Chem. Lett.; 13; 2003; 2191-2194, 1.94 g, 8.2 mmol), methanol (30 mL) and acetic acid (3 mL) was added (polystyrylmethyl)trimethylammonium cyanoborohydride (4.1 mmol/g, 1.9 g). The reaction mixture was heated for 5 min at 120° C. using microwave single node heating. The resin was filtered off and the solvent was removed by evaporation. There was obtained 2.85 g (99%) of 1-[1-(diphenylmethyl)azetidin-3-yl]piperidine-4-carboxamide. 1H NMR (500 MHz, CDCl3): 1.6-1.9 (m, 6H), 2.1-2.2 (m, 1H), 2.7-2.8 (d, 2H), 2.9-3.0 (m, 3H), 3.4 (t, 2H), 4.4 (s, 1H), 5.7-5.8 (b, 1H), 6.2 (b, 1H), 7.2 (t, 2H), 7.2-7.3 (t, 4H), 7.4 (d, 4H); LCMS: m/z 350 (M+1)+.

Workup

temperatureheating
filtrationThe resin was filtered off
customthe solvent was removed by evaporation

Sources & evidence

ORD record: ord-65e4207cbbc24a74b8fd15e4608a411d
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08106208B2

Reaction notes

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