Potassium Iodide → 3-Methoxy-4-[3-(1-pyrrolidinyl)propoxy]-benzoic acid Hydrochloride

HRID 1386298노트

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HRID 1386298 반응식
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[O:11][CH3:12].[N:13]1([CH2:18][CH2:19][CH2:20][Cl:21])[CH2:17][CH2:16][CH2:15][CH2:14]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C=O)C>[ClH:21].[CH3:12][O:11][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:2]=1[O:1][CH2:20][CH2:19][CH2:18][N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)[C:6]([OH:8])=[O:7]

참가 물질

6

반응물 4

HCID 4875Potassium IodideHCID 8468Vanillic AcidHCID 11430Potassium CarbonateHCID 113210281-(3-Chloropropyl)-pyrrolidine

생성물 1

HCID 248202363-Methoxy-4-[3-(1-pyrrolidinyl)propoxy]-benzoic acid Hydrochloride수율 77.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
100 °C

실험 절차

A mixture of 4-hydroxy-3-methoxybenzoic acid (8.4 g, 50 mmol), 3-(pyrrolidin-1-yl)propyl chloride (14.75 g, 0.1 mol), (prepared according to J. Am. Chem. Soc. 1955, 77. 2272), potassium carbonate (13.8 g, 0.1 mol) and potassium iodide (1.66 g, 10 mmol) in DMF (150 ml) was stirred and heated at 100° C. for 3 hours. The mixture was allowed to cool and the insolubles were removed by filtration and the volatiles were removed from the filtrate by evaporation. The residue was dissolved in ethanol (75ml), 2M aqueous sodium hydroxide (75 ml) was added and the mixture was heated at 90° C. for 2 hours. The mixture was concentrated by evaporation, acidified with concentrated hydrochloric acid, washed with ether and then subjected to purification on a Diaion (trade mark of Mitsubishi) HP20SS resin column, eluting with water and then with a gradient of methanol (0 to 25%) in dilute hydrochloric acid (pH2.2). The methanol was removed by evaporation and the aqueous residue was freeze dried to give 3-methoxy-4-(3-(pyrrolidin-1-yl)propoxy)benzoic acid hydrochloride (12.2 g, 77%).

후처리

  1. temperatureto cool
  2. customthe insolubles were removed by filtration
  3. customthe volatiles were removed from the filtrate by evaporation
  4. dissolutionThe residue was dissolved in ethanol (75ml)
  5. addition2M aqueous sodium hydroxide (75 ml) was added
  6. temperaturethe mixture was heated at 90° C. for 2 hours
  7. concentrationThe mixture was concentrated by evaporation
  8. washwashed with ether
  9. customsubjected to purification on a Diaion (trade mark of Mitsubishi) HP20SS resin column
  10. washeluting with water
  11. customThe methanol was removed by evaporation
  12. customdried

출처 및 근거

ORD 기록
ord-14daca9212164ccbad684da1e563796c
출처 데이터셋
uspto-grants-2001_07
특허 번호
US06265411B1

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