Formaldehyde → 2-(Piperidinomethyl)-1-Naphthol

HRID 37689Notes

Reaction equation

[C:1]1([OH:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[NH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.[CH2:18]=O>>[N:12]1([CH2:18][C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[C:1]=2[OH:11])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

Reactant 3

HCID 712Formaldehyde

HCID 70051-Naphthol

HCID 8082Piperidine

Product 1

HCID 2412412-(Piperidinomethyl)-1-NaphtholYield 45%

Procedure

Brown (Bull. Natl. Inst. Sci. India, No. 31, 167-178, 1965) discloses the following reaction scheme: Mannich reaction of 1-naphthol with piperidine and formaldehyde afforded 2-(piperidinomethyl)-1-naphthol in a yield of 45%. Reduction of 2-(piperidinomethyl)-1-naphthol in the presence of H2 /Pd/SrCO3 afforded 2-methyl-1-naphthol in a yield of 85%.

Workup

customthe following reaction scheme

Sources & evidence

ORD record: ord-734d68d293cd4cf08ab175f2026e880e
Source dataset: uspto-grants-1995_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05420362

Reaction notes

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