Benzoyl chloride → HCID 11739497, compound

HRID 1822017Notes

Reaction equation

[C:1]([Cl:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:10][N:11]1[CH2:16][CH2:15][CH:14]([O:17][C:18]2[CH:19]=[C:20]([NH2:24])[CH:21]=[CH:22][CH:23]=2)[CH2:13][CH2:12]1>O1CCOCC1>[ClH:9].[CH3:10][N:11]1[CH2:12][CH2:13][CH:14]([O:17][C:18]2[CH:19]=[C:20]([NH:24][C:1](=[O:8])[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:21]=[CH:22][CH:23]=2)[CH2:15][CH2:16]1

Participants

Conditions

Temperature: 110 °C

Procedure

Add benzoyl chloride (0.062 mL, 0.534 mmol) to a solution of 3-(1-methyl-piperidin-4-yloxy)-phenylamine (preparation 28, 102 mg, 0.494 mmol) in dioxane (3.5 mL) in a sealed tube and heat at 110° C. for 2 hr. Purification by SCX column, eluting with ammonia (2.0 N in methanol) gives the title compound as the free base (137 mg, 91%). Dissolve the residue in diethyl ether and treat with ethereal hydrogen chloride (1.0 M). Triturate the resulting gum with ether to give the title compound as the hydrochloride salt (139 mg, off-white solid). Mass spectrum (free base, ion spray): m/z=311.2 (M+1), 1H NMR (free base, CDCl3): 7.97 (bs, N—H), 7.85-7.82 (m, 2H), 7.52 (tt, J=1.3 Hz, 7.3 Hz, 1H), 7.49-7.42 (m, 3H), 7.22 (t, J=8.1 Hz, 1H), 7.05 (d, J=8.1 Hz, 1H), 6.69 (dd, J=2.1 Hz, 8.3 Hz, 1H), 4.38-4.30 (bm, 1H), 2.72-2.62 (bm, 2H), 2.35-2.23 (bm, 5H), 2.04-1.96 (bm, 2H), 1.89-1.79 (bm, 2H). Analysis calculated for C19H23ClN2O2.0.6H2O: C, 63.80; H, 6.82; N, 7.83. Found C, 63.67; H, 6.62; N, 7.83.

Workup

customPurification by SCX column
washeluting with ammonia (2.0 N in methanol)

Sources & evidence

ORD record: ord-ef03ae83bd2944ddae27e86e5b7682b5
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07608629B2

Reaction notes

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