Potassium Carbonate → HCID 22254655, compound

HRID 1611661Notes

Reaction equation

F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[NH2:11][CH:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])[CH2:14][CH2:13]1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[N+:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:11][CH:12]1[CH2:13][CH2:14][N:15]([C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])[CH2:16][CH2:17]1)([O-:10])=[O:9]

Participants

Conditions

Temperature: 100 °C

Procedure

A suspension of 2-fluoronitrobenzene (3.52 g, 25 mmol), 4-amino-1-(phenylmethyloxycarbonyl)piperidine† (4.0 g, 17 mmol) and potassium carbonate (64 g, 19 mmol) in DMSO (25 ml) was heated to 100° C. After 5 h the mixture was poured into ice/water and the resulting yellow solid was collected by filtration and washed with water. The solid was dried to give the title compound as a yellow solid (5.69 g, 16 mmol); NMR: 1.6 (m, 2H), 2.1 (d, 2H), 3.1 (t, 2H), 3.7 (m, 1H), 4.1 (d, 2H), 5.2 (s, 2H), 6.7 (t, 1H), 6.9 (d, 1H), 7.3-7.5 (m, 6H), 8.1 (d, 1H) and 8.2 (dd, 1H); MS: 356.

Workup

filtrationthe resulting yellow solid was collected by filtration
washwashed with water
customThe solid was dried

Sources & evidence

ORD record: ord-9cd419fe23424e92a6ea9eb36308787c
Source dataset: uspto-grants-2006_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06989393B2

Reaction notes

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