Propionic Acid → N-(4-Bromo-5,6,7,8-tetrahydroisoquinolin-8-yl)propionamide

HRID 714041

反応式

HRID 714041 の反応式
[Br:1][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH:7]([NH2:12])[C:6]=2[CH:5]=[N:4][CH:3]=1.[C:13](O)(=[O:16])[CH2:14][CH3:15].CCN=C=NCCCN(C)C.OP([O-])(O)=O.[K+]>C(Cl)Cl>[Br:1][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH:7]([NH:12][C:13](=[O:16])[CH2:14][CH3:15])[C:6]=2[CH:5]=[N:4][CH:3]=1

参加物

6

反応物 4

HCID 1032Propionic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 516951Monobasic potassium phosphateHCID 717433794-Bromo-5,6,7,8-tetrahydroisoquinolin-8-amine

生成物 1

HCID 86685953N-(4-Bromo-5,6,7,8-tetrahydroisoquinolin-8-yl)propionamide収率 92.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a stirred black solution of (rac)-4-bromo-5,6,7,8-tetrahydroisoquinolin-8-amine (317 mg, 1.4 mmol) and propionic acid (115 μL, 1.54 mmol) in CH2Cl2 (7.0 mL) at 0° C. was added EDCI (295 mg, 1.54 mmol), stirring was continued over night and the reaction mixture was allowed to warm up to RT. The reaction mixture was poured on aq. 10% KH2PO4 solution followed by extraction with AcOEt (3×). The organic phases were washed once with aq. 10% KH2PO4, aq. sat. NaHCO3 and with aq. sat. NaCl solution. The combined organic phases were dried over Na2SO4, filtered, evaporated and purified by precipitation CH2Cl2/n-pentane to afford the title compound (365 mg, 92%) as light brown solid. MS: 283.0 (M+H+, 1 Br).

後処理

  1. waitwas continued over night
  2. extractionfollowed by extraction with AcOEt (3×)
  3. washThe organic phases were washed once with aq. 10% KH2PO4, aq. sat. NaHCO3 and with aq. sat. NaCl solution
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. custompurified by precipitation CH2Cl2/n-pentane

出典と根拠

ORDレコード
ord-66872d1dad244e2ead41f8752fdb9ccc
出典データセット
uspto-grants-2015_11
特許番号
US09187429B2

関連ノート

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