Methylamine → Methyl-(1-propyl-naphthalen-2-ylmethyl)amine

HRID 1711813ノート

反応式

HRID 1711813 の反応式
[CH3:1][NH2:2].[CH2:3]([C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][C:7]=1[CH:16]=O)[CH2:4][CH3:5].[BH4-].[Na+]>CO>[CH3:1][NH:2][CH2:16][C:7]1[CH:8]=[CH:9][C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:6]=1[CH2:3][CH2:4][CH3:5]

参加物

5

反応物 3

HCID 6329MethylamineHCID 12014521-Propyl-naphthalene-2-carbaldehydeHCID 4311764Sodium borohydride

生成物 1

HCID 59456959Methyl-(1-propyl-naphthalen-2-ylmethyl)amine収率 89%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A solution of 2.0 M methylamine in methanol (20 mL) was added to 1-propyl-naphthalene-2-carbaldehyde (0.983 g, 4.95 mmol) under N2 and allowed to stir for 18 h. The solution was concentrated under reduced pressure. Then the resulting dark yellow oil was solvated in EtOH (20 mL) under N2. To the solution was added NaBH4 (0.187 g, 4.95 mmol) and the mixture allowed to stir for 6.5 h. The reaction was concentrated under reduced pressure, then solvated in 1 N NaOH (20 mL) and extracted with Et2O (3×50 mL). The organics were combined, washed with brine (2×100 mL), dried over Na2SO4, filtered and concentrated to yield the title compound (0.94 g, 89%) as a yellow oil: 1H NMR (300 MHz, DMSO-d6) δ 7.87-7.73 (m, 4H), 7.51-7.43 (m, 3H), 3.53 (m, 1H), 2.09 (s, 3H), 1.70-1.52 (m, 2H), 1.26-1.12 (m, 2H), 0.87-0.79 (m, 3H).

後処理

  1. concentrationThe solution was concentrated under reduced pressure
  2. stirringto stir for 6.5 h
  3. concentrationThe reaction was concentrated under reduced pressure
  4. extractionextracted with Et2O (3×50 mL)
  5. washwashed with brine (2×100 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-9905f4eb812845868f910e505b9d6b6b
出典データセット
uspto-grants-2010_09
特許番号
US07790709B2

反応ノート

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