p-Fluoronitrobenzene → HCID 1472673, compound

HRID 905664Notes

Reaction equation

HRID 905664 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][CH:3]=1.Cl.[NH:12]1[CH2:17][CH2:16][C:15](=O)[CH2:14][CH2:13]1.C(=O)([O-])[O-].[K+].[K+].[H-].[Na+].C(OP([CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])(OCC)=O)C>C1COCC1>[CH2:39]([O:38][C:36](=[O:37])[CH2:35][CH:15]1[CH2:16][CH2:17][N:12]([C:2]2[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][CH:3]=2)[CH2:13][CH2:14]1)[CH3:40]

Participants

7

Reactant 5

HCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 30848514-Piperidone hydrochloride

Product 1

HCID 1472673HCID 1472673, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

4-Fluoronitrobenzene and piperidin-4-one hydrochloride were allowed to undergo the reaction in THF in the presence of potassium carbonate. The resulting compound was allowed to react with sodium hydride and ethyl diethylphosphonoacetate in THF. The resulting compound was subjected to catalytic hydrogenation in the same manner as shown in Reference Example 3 to obtain [1-(4-aminophenyl)piperidin-4-yl]acetic acid ethyl ester. NMR2: 1.27 (3 H, t, J=7.2 Hz), 2.33 (2 H, d, J=7.2 Hz), 6.66-6.89 (2H, m).

Sources & evidence

ORD record
ord-58458b34f7474e44be48b289b3e3a63b
Source dataset
uspto-grants-2011_09
Patent number
US08012959B2

Reaction notes

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