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Phenylacetyl chloride → 6-[4-(Benzylcarbonylamino)benzyloxy]-2-[(N,N-dimethylamino)methyl]tetralin

HRID 1242881
ノート
印刷プレビュー

反応式

HRID 1242881 の反応式
C1COCC1.[C:6]1([CH2:12][C:13](Cl)=[O:14])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[NH2:16][C:17]1[CH:38]=[CH:37][C:20]([CH2:21][O:22][C:23]2[CH:24]=[C:25]3[C:30](=[CH:31][CH:32]=2)[CH2:29][CH:28]([CH2:33][N:34]([CH3:36])[CH3:35])[CH2:27][CH2:26]3)=[CH:19][CH:18]=1.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C.N1C=CC=CC=1>[CH2:12]([C:13]([NH:16][C:17]1[CH:38]=[CH:37][C:20]([CH2:21][O:22][C:23]2[CH:24]=[C:25]3[C:30](=[CH:31][CH:32]=2)[CH2:29][CH:28]([CH2:33][N:34]([CH3:35])[CH3:36])[CH2:27][CH2:26]3)=[CH:19][CH:18]=1)=[O:14])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 7679Phenylacetyl chlorideHCID 8028TetrahydrofuranHCID 516892Sodium BicarbonateHCID 219397226-(4-Aminobenzyloxy)-2-[(N,N-dimethylamino)methyl]tetralin

生成物 1

HCID 219400516-[4-(Benzylcarbonylamino)benzyloxy]-2-[(N,N-dimethylamino)methyl]tetralin収率 42.3%

試薬・触媒・溶媒 2

HCID 1049
Pyridine
溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

THF solution (1 ml) of phenylacetyl chloride (200 mg) was added dropwise to pyridine solution (6 ml) of 6-[(4-aminobenzyl)oxy]-2-[(N,N-dimethylamino)methyl]tetralin (300 mg) under ice-cooling, which was stirred for 15 minutes. After stirring at room temperature for further 15 minutes, saturated sodium bicarbonate solution was added to the reaction mixture, and extraction was conducted using ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride solution, dried, and then concentrated. The residue was purified using alumina column chromatography (development solvent; hexane˜hexane:ethyl acetate=2:1), and recrystallized to give the titled compound (175 mg).

後処理

  1. temperaturecooling
  2. stirringAfter stirring at room temperature for further 15 minutes
  3. washThe organic layer was washed with water and saturated aqueous sodium chloride solution
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified
  7. customrecrystallized

出典と根拠

ORDレコード
ord-98a33b5091a549569949afc7ea2391ef
出典データセット
uspto-grants-2006_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07115750B1

反応ノート

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