1-Naphthaldehyde → 1-{(S)-[methyl-((S)-1-phenyl-ethyl)-amino]-naphthalen-1-yl-methyl}-naphthalen-2-ol

HRID 735395

Reaction equation

[C:1]1([CH:11]=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[CH3:13][NH:14][C@@H:15]([CH3:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[CH:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][C:24]=1[OH:33]>CO>[CH3:13][N:14]([C@@H:11]([C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1)[C:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][C:24]=1[OH:33])[C@H:15]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH3:22]

Participants

Conditions

Temperature: 85 °C

Procedure

1-Naphthaldehyde (2.7 mL, 20 mmol), (S)-(−)-N,α-dimetylbenzylamine (2.60 g, 19 mmol) and 2-naphthol (2.43 g, 16 mmol) are charged into a 25 mL flask with a magnetic stirring bar. The mixture is heated to 85° C. and stirred for 72 h. After the system is cooled to RT, MeOH (5 mL) is added and the precipitated product is collected by filtration, washed with MeOH (5 mL) and dried to afford 1-{(S)-[methyl-((S)-1-phenyl-ethyl)-amino]-naphthalen-1-yl-methyl}-naphthalen-2-ol as white crystals (about 51% yield): 1H NMR (500 MHz, CDCl3) δ 14.01 (br s, 1H), 7.77-7.02 (m, 18H), 6.45 (s, 1H), 4.40 (br s, 1H), 1.95 (s, 3H), 1.65 (br s, 3H); MS (EI) m/z (rel intensity) 418 (M++1), 283, 141, 136; HRMS (EI) Calcd for C30H28NO (M++1): 418.2171, found 418.2135.

Workup

temperatureAfter the system is cooled to RT
filtrationthe precipitated product is collected by filtration
washwashed with MeOH (5 mL)
customdried

Sources & evidence

ORD record: ord-2f55e3e8972c41f694b8b10764232ea7
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07592487B2

Linked notes

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