4-Amino-5-chloro-2-methoxybenzoic acid → 4-Piperidinylmethyl 4-amino-5-chloro-2-methoxybenzoate

HRID 611771

반응식

HRID 611771 반응식
[NH2:1][C:2]1[C:10]([Cl:11])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([O:12][CH3:13])[CH:3]=1.C([N:21]1[CH2:26][CH2:25][CH:24]([CH2:27]O)[CH2:23][CH2:22]1)C1C=CC=CC=1>C1COCC1.C([Li])CCC>[NH:21]1[CH2:26][CH2:25][CH:24]([CH2:27][O:7][C:6](=[O:8])[C:5]2[CH:9]=[C:10]([Cl:11])[C:2]([NH2:1])=[CH:3][C:4]=2[O:12][CH3:13])[CH2:23][CH2:22]1

참가 물질

5

반응물 2

HCID 816264-Amino-5-chloro-2-methoxybenzoic acidHCID 736802(1-Benzylpiperidin-4-yl)methanol

생성물 1

HCID 226627574-Piperidinylmethyl 4-amino-5-chloro-2-methoxybenzoate수율 109.1%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 178418339Butyllithium용매

실험 절차

1,1-carbonyldiimidazole (0.8 g., 0.005 mol) was added to a solution of 4-amino-5-chloro-2-methoxy-benzoic acid (1 g, 5 mmol) in THF (20 ml) and the reaction mixture was stirred at room temperature for about 30 minutes. The solvent was evaporated and the residue was taken up in H2O and extracted into ethyl acetate (3×20 ml). The organic phases were collected, dried and evaporated to dryness. The obtained solid residue was dissolved in THF (10 ml) and dropped into a solution of 1-benzylpiperidin-4-yl-methanol [J. Med. Chem. (1992), 35, 4344], (1 g, 5 mmol) in THF (10 ml) and butyllithium (1.6 M in hexane; 3 ml), maintained at 0° C. The reaction mixture was further stirred at room temperature for 1 hour. The solvent was evaporated and the residue was taken up into H2O and extracted into ethyl acetate. The organic extracts were dried and evaporated to give the desired product as a pale yellow oil, (1.63 g).

후처리

  1. customThe solvent was evaporated
  2. extractionextracted into ethyl acetate (3×20 ml)
  3. customThe organic phases were collected
  4. customdried
  5. customevaporated to dryness
  6. dissolutionThe obtained solid residue was dissolved in THF (10 ml)
  7. temperaturemaintained at 0° C
  8. stirringThe reaction mixture was further stirred at room temperature for 1 hour
  9. customThe solvent was evaporated
  10. extractionextracted into ethyl acetate
  11. customThe organic extracts were dried
  12. customevaporated

출처 및 근거

ORD 기록
ord-7fd99fa515d346f1987bde2943c9f9dd
출처 데이터셋
uspto-grants-1999_12
특허 번호
US06002009

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