p-Fluoronitrobenzene → HCID 12050748, compound

HRID 1473015Notes

Reaction equation

NC1C=CC(N2CCC(NC(=O)OC(C)(C)C)CC2)=CC=1.[NH:22]1[CH2:27][CH2:26][CH:25]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[CH2:24][CH2:23]1.F[C:37]1[CH:42]=[CH:41][C:40]([N+:43]([O-:45])=[O:44])=[CH:39][CH:38]=1>>[N+:43]([C:40]1[CH:41]=[CH:42][C:37]([N:22]2[CH2:23][CH2:24][CH:25]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:32])([CH3:34])[CH3:33])[CH2:26][CH2:27]2)=[CH:38][CH:39]=1)([O-:45])=[O:44]

Participants

Reactant 3

HCID 9590p-Fluoronitrobenzene

HCID 7238334-(N-Boc-amino)piperidine

HCID 12050749Carbamic acid, N-[1-(4-aminophenyl)-4-piperidinyl]-, 1,1-dimethylethyl ester

Product 1

HCID 12050748HCID 12050748, compound

Procedure

tert-Butyl (1-(4-aminophenyl)piperidin-4-yl)carbamate (G29) can be prepared by nucleophilic aromatic substitution of commercially available tert-butyl piperidin-4-ylcarbamate (G26) and 1-fluoro-4-nitrobenzene (G27) under thermal conditions to give tert-butyl (1-(4-nitrophenyl)piperidin-4-yl)carbamate (G28). Reduction of G28 with hydrogen in the presence of a catalyst, for example 10% palladium on charcoal gives tert-butyl (1-(4-aminophenyl)piperidin-4-yl)carbamate (G29).

Sources & evidence

ORD record: ord-d86f83cd6ed746b99ee9545d2f9f9325
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09012461B2

Reaction notes

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