Benzylamine → HCID 22220589, compound

HRID 1061426Notes

Reaction equation

[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:13][CH:12](OS(C)(=O)=O)[CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH2:19]([NH2:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>O>[CH2:19]([NH:26][CH:12]1[CH2:13][N:10]([C:7]2[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[CH2:11]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Methanesulfonic acid 1-(4-nitro-phenyl)-azetidin-3-yl ester (which was obtained in Example 397) (14.32 g, 52.6 mmol) was added to neat benzyl amine (56 mL, 526 mmol) and stirred at 100° C. for 2 days. Water (200 mL) was added and the resultant precipitate was collected and partitioned between ethyl acetate and saturated aqueous NaHCO3. The aqueous layer was washed with ethyl acetate (2×50 mL). The organic extract was dried over anhydrous sodium sulfate, filtered, and concentrated. The solid was washed with diethyl ether and dried to give 12.1 g of the desired product as an orange solid; 1H NMR (300 MHz, CDCl3) δ1.66 (brs, 1H), 3.72 (m, 2H), 3.82 (s, 2H), 3.89 (m, 1H), 4.19 (t, 2H, J=7.77 Hz), 6.29 (d, 2H, J=9.12 Hz), 7.34 (m, 5H), 8.07 (d, 2H, J=9.18 Hz); MS (ES) m/z: 283.8 (MH+); Anal. Calcd. for C16H17N3O2: C, 67.83; H, 6.05; N, 14.83. Found: C, 67.59; H, 6.04; N, 14.79.

Workup

customthe resultant precipitate was collected
custompartitioned between ethyl acetate and saturated aqueous NaHCO3
washThe aqueous layer was washed with ethyl acetate (2×50 mL)
extractionThe organic extract
dry with materialwas dried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated
washThe solid was washed with diethyl ether
customdried

Sources & evidence

ORD record: ord-aba10d27986e448282b5e5e460184c33
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06525202B2

Reaction notes

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