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

HRID 1944829ノート

反応式

HRID 1944829 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-2f5445b9caa247c28f86f08944584834
出典データセット
uspto-grants-2013_03
特許番号
US08394902B2

反応ノート

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