Benzylamine → 3-Benzylamino-1-indanol

HRID 65838

반응식

HRID 65838 반응식
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12](=[O:19])[CH2:11]1>CCOCC>[CH2:1]([NH:8][CH:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]([OH:19])[CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 7504BenzylamineHCID 117459123-Bromo-1-indanone

생성물 1

HCID 227560943-Benzylamino-1-indanol

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

실험 절차

Cool a solution of benzylamine (3.22 g.) in dry ether (25 ml.) to below 0° C. With stirring under nitrogen add a cooled (below 0° C.) solution of 3-bromo-1-indanone (3.17 g.) in ether (25 ml.) dropwise over 1.5 hours. Store the reaction under nitrogen at -10° C. for one day. Quickly filter the cold solution and add it cold to a stirring solution of one molar borane in tetrahydrofuran (60 ml.) below 0° C. and under nitrogen. Stir the solution for 18 hours at room temperature. Carefully add a solution of water (3.24 ml.) in tetrahydrofuran (20 ml.) dropwise, followed by 8.0 ml. of 5M isopropanolic --HCl, and continue stirring overnight. Store the reaction at -10° C. overnight, then filter the precipitate through filter-aid. Extract the dry solid mixture with methanol-methylene chloride, filter and evaporate the solvents in vacuo. Triturate the resulting solid with cold ethyl acetate, filter and dry to obtain 2.36 g. of the title product as the hydrochloride salt, m.p. 233-235°. λmaxKBr 3.0 μ (OH).

후처리

  1. additionadd
  2. customStore the reaction under nitrogen at -10° C. for one day
  3. filtrationQuickly filter the cold solution
  4. additionadd it cold to a stirring solution of one molar borane in tetrahydrofuran (60 ml.) below 0° C.
  5. stirringStir the solution for 18 hours at room temperature
  6. additionCarefully add a solution of water (3.24 ml.) in tetrahydrofuran (20 ml.) dropwise
  7. stirringof 5M isopropanolic --HCl, and continue stirring overnight
  8. customStore the reaction at -10° C. overnight
  9. filtrationfilter the precipitate
  10. filtrationthrough filter-aid
  11. extractionExtract the dry solid mixture with methanol-methylene chloride
  12. filtrationfilter
  13. customevaporate the solvents in vacuo
  14. customTriturate the resulting solid with cold ethyl acetate
  15. filtrationfilter
  16. customdry
  17. customto obtain 2.36 g

출처 및 근거

ORD 기록
ord-d1550dc8f84e476d99984a492aceb7c5
출처 데이터셋
uspto-grants-1978_12
특허 번호
US04129561

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