Dimethylamine → 1-(7-Dimethylaminomethyl-1,2,4,5-tetrahydro-3-benzazepin-3-yl)-2,2,2-trifluoroethanone

HRID 644352ノート

反応式

HRID 644352 の反応式
[CH3:1][NH:2][CH3:3].[F:4][C:5]([F:22])([F:21])[C:6]([N:8]1[CH2:14][CH2:13][C:12]2[CH:15]=[CH:16][C:17]([CH:19]=O)=[CH:18][C:11]=2[CH2:10][CH2:9]1)=[O:7].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>C1COCC1.C(O)(=O)C>[CH3:1][N:2]([CH2:19][C:17]1[CH:16]=[CH:15][C:12]2[CH2:13][CH2:14][N:8]([C:6](=[O:7])[C:5]([F:22])([F:4])[F:21])[CH2:9][CH2:10][C:11]=2[CH:18]=1)[CH3:3]

参加物

7

反応物 4

HCID 674DimethylamineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 582779543-(2,2,2-trifluoro-acetyl)-2,3,4,5-tetrahydro-1H-3-benzazepine-7-carbaldehyde

生成物 1

HCID 866042901-(7-Dimethylaminomethyl-1,2,4,5-tetrahydro-3-benzazepin-3-yl)-2,2,2-trifluoroethanone

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

11.7 mL (23.4 mmol) of a 2 M dimethylamine solution in THF were added to a solution of 4.5 g (16.59 mmol) 3-(2,2,2-trifluoro-acetyl)-2,3,4,5-tetrahydro-1H-3-benzazepine-7-carbaldehyde in 150 mL THF and the solution was adjusted to pH 5 with 1 mL glacial acetic acid. After 30 min 4.62 g (21.79 mmol) sodium triacetoxyborohydride were added and the reaction mixture was stirred overnight at RT. The reaction solution was carefully combined with saturated NaHCO3 solution, stirred for 30 min, exhaustively extracted with EtOAc, the organic phase was separated off and dried over Na2SO4. After the desiccant and solvent had been eliminated the desired product was obtained, which was further reacted without purification.

後処理

  1. stirringstirred for 30 min
  2. extractionexhaustively extracted with EtOAc
  3. customthe organic phase was separated off
  4. dry with materialdried over Na2SO4
  5. customwas obtained
  6. customwhich was further reacted without purification

出典と根拠

ORDレコード
ord-04b167256c194d23b617a099fc2f671c
出典データセット
uspto-grants-2010_04
特許番号
US07700589B2

反応ノート

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