p-Toluidine → para-methyl 4-Anilino-1-Boc-piperidine

HRID 1726307Notes

Reaction equation

[C:1]([N:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[NH2:15][C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=1>>[C:4]([O:3][C:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=2)[CH2:10][CH2:9]1)=[O:2])([CH3:7])([CH3:6])[CH3:5]

Participants

Reactant 2

HCID 7813p-Toluidine

HCID 735900tert-Butyl 4-oxopiperidine-1-carboxylate

Product 1

HCID 22557837para-methyl 4-Anilino-1-Boc-piperidineYield 96.3%

Procedure

Using general procedure A, 1-Boc-4-piperidone (665 mg, 3.34 mmol) and p-toluidine (322 mg, 3.01 mmol) gave 4-p-tolylamino-piperidine-1-carboxylic acid tert-butyl ester as an off-white solid (842 mg, 96%).

Sources & evidence

ORD record: ord-7d84a38f8fc947569a9cccec8cfad494
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07491735B2

Reaction notes

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