4-[1-(Naphthalene-2-carbonyl)-piperidin-4-ylamino]benzoic acid tert-butyl ester → 4-[1-(Naphthalene-2-carbonyl)piperidin-4-ylamino]benzoic acid

HRID 1274150Notes

Reaction equation

C([O:5][C:6](=[O:32])[C:7]1[CH:12]=[CH:11][C:10]([NH:13][CH:14]2[CH2:19][CH2:18][N:17]([C:20]([C:22]3[CH:31]=[CH:30][C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[CH:23]=3)=[O:21])[CH2:16][CH2:15]2)=[CH:9][CH:8]=1)(C)(C)C>Cl>[CH:23]1[C:24]2[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:30]=[CH:31][C:22]=1[C:20]([N:17]1[CH2:16][CH2:15][CH:14]([NH:13][C:10]2[CH:9]=[CH:8][C:7]([C:6]([OH:32])=[O:5])=[CH:12][CH:11]=2)[CH2:19][CH2:18]1)=[O:21]

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of (10) (0.039 g, 0.09 mmol) in HCl (5 mL, 4M in 1,4-dioxane) was capped with a drying tube and stirred at 25° C. for 12 h. The reaction mixture was concentrated to give a white solid residue (0.02 g, 57%); 1H NMR (DMSO) δ 7.98 (m, 4H), 7.66 (d, 2H, J=8.7), 7.55 (m, 3H), 6.65 (d, 2H, J=8.8), 4.41 (m, 2H), 3.67 (m, 1H), 3.15 (m, 2H), 1.95 (m, 2H), 1.40 (m, 2H); 13C NMR (DMSO) δ 169.0, 167.4, 151.1, 133.6, 133.1, 132.3, 131.1, 128.3, 128.1, 127.7, 127.1, 126.8, 126.1, 124.3, 117.3, 111.6, 48.7, 45.9, 31.2; HRMS (FAB) m/z 375.1693 (M+H)+ (C23H22N2O3 requires 375.1709); Anal. (C23H22N2O3 ·2HCl·4H2O) C, H, N.

Workup

concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record: ord-ec57574fd864453986a1094304af4250
Source dataset: uspto-grants-2000_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06156758

Reaction notes

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