3-Piperidinol, 1-methyl- → 3-Nitro-7,8-dihydro-6H-5-oxa-9-aza-benzocycloheptene-9-carboxylic acid 1-methyl-piperidin-3-yl ester

HRID 1687811Notes

Reaction equation

HRID 1687811 reaction equation
Cl[CH2:2][CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][C:12]([N+:14]([O-:16])=[O:15])=[CH:13][C:8]=2[O:7][C:6]1=[O:17].[CH3:18][N:19]1[CH2:24][CH2:23][CH2:22][CH:21]([OH:25])[CH2:20]1>>[CH3:18][N:19]1[CH2:24][CH2:23][CH2:22][CH:21]([O:25][C:6]([N:5]2[C:9]3[CH:10]=[CH:11][C:12]([N+:14]([O-:16])=[O:15])=[CH:13][C:8]=3[O:7][CH2:2][CH2:3][CH2:4]2)=[O:17])[CH2:20]1

Participants

3

Reactant 2

HCID 980163-Piperidinol, 1-methyl-HCID 672636543-(3-chloro-propyl)-6-nitro-3H-benzoxazol-2-one

Product 1

HCID 672638013-Nitro-7,8-dihydro-6H-5-oxa-9-aza-benzocycloheptene-9-carboxylic acid 1-methyl-piperidin-3-yl ester

Procedure

3-Nitro-7,8-dihydro-6H-5-oxa-9-aza-benzocycloheptene-9-carboxylic acid 1-methyl-piperidin-3-yl ester was prepared from 3-(3-chloro-propyl)-6-nitro-3H-benzoxazol-2-one and 1-methyl-piperidin-3-ol in an analogous manner to Example 1426a. Product isolated as a yellow oil (420 mg, 53%). LCMS (m/e) 336 (M+H); 1H-NMR (CDCl3, 400 MHz) δ 7.89-7.80 (m, 2H), 7.58-7.44 (m, 1H), 4.92-4.81 (m, 1H), 4.30-4.18 (m, 2H), 3.98-3.72 (m, 2H), 2.82-2.71 (m, 1H), 2.56-2.45 (m, 1H), 2.27 (s, 3H), 2.27-2.07 (m, 4H), 1.97-1.84 (m, 1H), 1.80-1.66 (m, 1H), 1.66-1.52 (m, 1H), 1.52-1.30 (m, 1H).

Sources & evidence

ORD record
ord-13b1df2165bb4127b492c5ac58bded5e
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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