Acetic Acid → [1-(3-Bromophenyl)-2-(4-morpholinyl)ethyl]methylamine

HRID 2114347ノート

反応式

HRID 2114347 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([C:8](=O)[CH2:9][N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[CH:5]=[CH:6][CH:7]=1.CN.[C:19]([BH3-])#[N:20].[Na+].C(O)(=O)C>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]([NH:20][CH3:19])[CH2:9][N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 176Acetic AcidHCID 6329MethylamineHCID 5003444Sodium cyanoborohydrideHCID 208237461-(3-Bromophenyl)-2-(4-morpholinyl)ethanone

生成物 1

HCID 57501274[1-(3-Bromophenyl)-2-(4-morpholinyl)ethyl]methylamine収率 100.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 1-(3-bromophenyl)-2-(4-morpholinyl)ethanone (7.8 g, 27.0 mmol) in THF (50 mL) was added methylamine (100 mL, 200 mmol, 2M solution in THF). After stirring for 15 min at room temperature, sodium cyanoborohydride (3.40 g, 54 mmol) was added followed by acetic acid (2 mL). The resultant mixture was stirred at RT for 5 days. The mixture was concentrated under reduced pressure. The residue was dissolved in ethyl acetate (200 mL) and washed with 5% NaHCO3 (200 mL) and brine (200 mL). The organic layer was dried (MgSO4) and concentrated to give [1-(3-bromophenyl)-2-(4-morpholinyl)ethyl]methylamine as yellow oil (8.10 g, 100%) which solidified after standing at room temperature. MS (ESI): 299.6 [M+H]+.

後処理

  1. concentrationThe mixture was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate (200 mL)
  3. washwashed with 5% NaHCO3 (200 mL) and brine (200 mL)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-af173e9b66af485e88b2a2aae1d99e84
出典データセット
uspto-grants-2008_10
特許番号
US07432258B2

反応ノート

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