1,3-Benzodioxole-5-carboxylic acid → 1,3-Benzodioxole-5-carboxamide, N-((4-(2-(1-pyrrolidinyl)ethoxy)phenyl)methyl)-

HRID 703529

반응식

HRID 703529 반응식
[N:1]1([CH2:6][CH2:7][O:8][C:9]2[CH:16]=[CH:15][C:12]([CH2:13][NH2:14])=[CH:11][CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:17]1[O:28][C:27]2[CH:26]=[CH:25][C:21]([C:22](Cl)=[O:23])=[CH:20][C:19]=2[O:18]1.C(O)(=O)C1C=CC2OCOC=2C=1.S(Cl)(Cl)=O>C(Cl)(Cl)Cl>[CH2:17]1[O:28][C:27]2[CH:26]=[CH:25][C:21]([C:22]([NH:14][CH2:13][C:12]3[CH:11]=[CH:10][C:9]([O:8][CH2:7][CH2:6][N:1]4[CH2:2][CH2:3][CH2:4][CH2:5]4)=[CH:16][CH:15]=3)=[O:23])=[CH:20][C:19]=2[O:18]1

참가 물질

6

반응물 4

HCID 71961,3-Benzodioxole-5-carboxylic acidHCID 24386Thionyl ChlorideHCID 27347491,3-Benzodioxole-5-carbonyl chlorideHCID 14425929(4-(2-(Pyrrolidin-1-yl)ethoxy)phenyl)methanamine

생성물 1

HCID 30788161,3-Benzodioxole-5-carboxamide, N-((4-(2-(1-pyrrolidinyl)ethoxy)phenyl)methyl)-수율 89.7%

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

To a cooled solution of 20.0 g of 4-[2-(1-pyrrolidinyl)ethoxy]benzylamine in 30 ml of chloroform was added 17.7 g of 3,4-methylenedioxybenzoyl chloride (which was prepared with 15.9 g of piperonylic acid and 65.3 g of thionyl chloride in the usual manner). The mixture was stirred at room temperature for 20 minutes and the solvent was evaporated. 150 ml of water was added to the residue and the mixture was washed with ethyl acetate. The aqueous layer was made alkaline with potassium carbonate and was extracted with ethyl acetate. The extract was washed with water, dried, and evaporated. The residue was washed with isopropyl ether to give 30.0 g of colorless crystals, which were recrystallized from ethyl acetate as colorless needles, m.p. 93.5°-94.5° C.

후처리

  1. customthe solvent was evaporated
  2. addition150 ml of water was added to the residue
  3. washthe mixture was washed with ethyl acetate
  4. extractionwas extracted with ethyl acetate
  5. washThe extract was washed with water
  6. customdried
  7. customevaporated
  8. washThe residue was washed with isopropyl ether

출처 및 근거

ORD 기록
ord-bc3aa1fa71ee41219775f90b89013820
출처 데이터셋
uspto-grants-1991_01
특허 번호
US04983633

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