Formaldehyde → 2-(Piperidinomethyl)-1-Naphthol

HRID 37684Notes

Reaction equation

HRID 37684 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.C=O.[NH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.[NH:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1>>[N:14]1([CH2:21][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])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.[O:23]1[CH2:24][CH2:25][N:20]([CH2:15][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])[CH2:21][CH2:22]1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 70051-NaphtholHCID 8082PiperidineHCID 8083Morpholine

Product 2

HCID 2412412-(Piperidinomethyl)-1-NaphtholHCID 3829501-Naphthalenol, 2-(4-morpholinylmethyl)-

Procedure

Anon. (USA) (Res. Discl., 236, 380 (Ger), 1983) discloses a Mannich reaction of 1-naphthol with formalin and piperidine or morpholine to yield 2-(piperidinomethyl)-1-naphthol or 2-(morpholinomethyl)-1-naphthol, respectively. These compounds were subjected to hydrogenolysis (Pd/C) whereby 2-methyl-1-naphthol was produced

Sources & evidence

ORD record
ord-845bb11cfab64d898e0390f7ee4a116c
Source dataset
uspto-grants-1995_05
Patent number
US05420362

Reaction notes

Loading…