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Ethanolamine → N-[1-(3,4-dimethoxyphenyl)-2-phenylethyl]-2-hydroxy-2-(2-chloropyrid-5-yl)-ethylamine

HRID 861439
ノート
印刷プレビュー

反応式

HRID 861439 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]([NH2:19])[CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([C:27](=[O:30])[CH2:28]Br)=[CH:23][N:22]=1.[BH4-].[Na+].C(CN)O>C(#N)C.C(OCC)(=O)C.C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]([NH:19][CH2:28][CH:27]([OH:30])[C:24]2[CH:25]=[CH:26][C:21]([Cl:20])=[N:22][CH:23]=2)[CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 700EthanolamineHCID 411116alpha-(3,4-Dimethoxyphenyl)benzeneethanamineHCID 4311764Sodium borohydrideHCID 194329212-Bromo-1-(6-chloropyridin-3-YL)ethanone

生成物 1

HCID 19704231N-[1-(3,4-dimethoxyphenyl)-2-phenylethyl]-2-hydroxy-2-(2-chloropyrid-5-yl)-ethylamine

試薬・触媒・溶媒 3

HCID 702
Ethanol
溶媒
HCID 6342Acetonitrile溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of α-(3,4-dimethoxyphenyl)-benzenee-thanamine (see Washburn et al., EP 0 659 737 A2 for the preparation of this compound) (257 mg, 1 mmol, 2 eq) in anhydrous acetonitrile (10 mL) is added a solution of 2-chloro-5-(2-bromoacetyl)pyridine (prepared as described in Example 3) (111 mg, 0.5 mmol) at 0° C. under a nitrogen atmosphere. The mixture is allowed to warm to room temperature and stirred for 1 h. To this mixture is added a solution of sodium borohydride (110 mg, 2.9 mmol, 5.8 eq) in abs. ethanol at room temperature. After one hour, the excess sodium borohydride is quenched with 1N HCl to pH 4.0 and then ethanol amine (0.28 mL, 4.5 mmol, 8 eq) is added. After stirring for 10 minutes, the mixture is diluted with ethyl acetate (30 mL). The organic layer is washed with brine, dried over anhydrous sodium sulfate and then concentrated. Purification by silica column gives the desired compound.

後処理

  1. customat room temperature
  2. waitAfter one hour
  3. customthe excess sodium borohydride is quenched with 1N HCl to pH 4.0
  4. stirringAfter stirring for 10 minutes
  5. washThe organic layer is washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. customPurification by silica column

出典と根拠

ORDレコード
ord-b87efb50b82d4c2b82c971c04f44b5c5
出典データセット
uspto-grants-1998_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05714506

反応ノート

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