Dichloromethane → N-[(1-{6-[(tert-Butylamino)methyl]pyridin-2-yl}-2-naphthyl)methyl]-2-methylaniline

HRID 1944829Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1944829
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][CH2:9][C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]=1[C:20]1[N:25]=[C:24]([CH:26]=O)[CH:23]=[CH:22][CH:21]=1.[C:28]([NH2:32])([CH3:31])([CH3:30])[CH3:29].[BH3-]C#N.[Na+].ClCCl>C(O)C>[C:28]([NH:32][CH2:26][C:24]1[N:25]=[C:20]([C:11]2[C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:18]=[CH:19][C:10]=2[CH2:9][NH:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[CH3:1])[CH:21]=[CH:22][CH:23]=1)([CH3:31])([CH3:30])[CH3:29]

Komponenten

6

Edukt 4

HCID 6344DichloromethaneHCID 6385Tert-ButylamineHCID 5003444Sodium cyanoborohydrideHCID 866633926-(2-{[(2-Methylphenyl)amino]methyl}-1-naphthyl)pyridine-2-carbaldehyde

Produkt 1

HCID 66795970N-[(1-{6-[(tert-Butylamino)methyl]pyridin-2-yl}-2-naphthyl)methyl]-2-methylaniline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 1.79 g (5.09 mmol) of 6-(2-{[(2-methylphenyl)amino]methyl}-1-naphthyl)pyridine-2-carbaldehyde, 1.85 g (25.4 mmol) of tert-butylamine and 0.641 g (10.2 mmol) of NaBH3CN in 100 ml of dry ethanol was stirred overnight at room temperature. The resulting mixture was evaporated to dryness. The product was isolated from the residue by flash chromatography on neutral alumina (eluent: dichloromethane, then dichloromethane-ether=1:1, vol.). Yield 1.10 g (53%) of yellowish oil. Anal. calc. for C28H31N3: C, 82.11; H, 7.63; N, 10.26. Found: C, 82.34; H, 7.79; N, 10.11. 1H NMR (CDCl3): 7.90 (d, J=8.6 Hz, 1H, 4-H in naphthyl), 7.88 (m, 1H, 8-H in naphthyl), 7.79 (m, 1H, 4-H in Py), 7.65 (d, J=8.6 Hz, 1H, 3-H in naphthyl), 7.38-7.48 (m, 4H, 3-H in Py and 5,6,7-H in naphthyl), 7.32 (m, 1H, 5-H in Py), 7.01-7.04 (m, 2H, 3,5-H in ortho-tolyl), 6.63 (m, 1H, 4-H in ortho-tolyl), 6.52 (m, 1H, 6-H in ortho-tolyl), 4.22 (m, 2H, Naph-CH2N), 4.01 (m, 2H, Py-CH2N), 3.50 (br. s, 2H, NH), 2.11 (s, 3H, Me in ortho-tolyl), 1.18 (s, 9H, tBu).

Aufarbeitung

  1. customThe resulting mixture was evaporated to dryness
  2. customThe product was isolated from the residue by flash chromatography on neutral alumina (eluent

Quellen und Nachweise

ORD-Eintrag
ord-2f5445b9caa247c28f86f08944584834
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08394902B2

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