4-Amino-1-methylpiperidine → HCID 11709785, compound

HRID 506249Notes

Reaction equation

HRID 506249 reaction equation
[C:1]1([C:7]2[O:8][C:9]3[C:15]([C:16]([OH:18])=O)=[CH:14][CH:13]=[CH:12][C:10]=3[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:19][CH:20]1[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]1>>[CH3:26][N:23]1[CH2:24][CH2:25][CH:20]([NH:19][C:16]([C:15]2[C:9]3[O:8][C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)=[N:11][C:10]=3[CH:12]=[CH:13][CH:14]=2)=[O:18])[CH2:21][CH2:22]1

Participants

3

Reactant 2

HCID 27375314-Amino-1-methylpiperidineHCID 118067277-Benzoxazolecarboxylic acid, 2-phenyl-

Product 1

HCID 11709785HCID 11709785, compoundYield 58%

Procedure

N-(1-Methylpiperidin-4-yl)-2-phenylbenzoxazole-7-carboxamide was prepared from 2-phenylbenzoxazole-7-carboxylic acid and 4-amino-1-methylpiperidine using the method outlined in Step C of Example 7. This compound was obtained in 58% yield and obtained as a white solid: mp 209-210° C.; 1H NMR (300 MHz, CDCl3) δ 8.22 (m, 1H), 8.21 (dd, J=5.7, 1.8 Hz, 1H), 8.10 (dd, J=8.1, 0.9 Hz, 1H), 7.91 (dd, J=9.9, 1.2 Hz, 1H), 7.64-7.54 (m, 3H), 7.48 (t, J=7.8, 1H), 4.26-4.17 (m, 1H), 2.93 (d, J=11.4 Hz, 2H), 2.46 (s, 3H), 2.30 (t, J=11.1 Hz, 2H), 2.22-2.17 (m, 2H), 1.85-1.73 (m, 2H); MS (ESI) m/z 336 [M+H]+

Workup

  1. customThis compound was obtained in 58% yield
  2. customobtained as a white solid

Sources & evidence

ORD record
ord-d47a0e2d4455430490ea8f93896b55c1
Source dataset
uspto-grants-2010_08
Patent number
US07781430B2

Reaction notes

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