Acetic Acid → 1-Amino-5,6,7,8-tetrahydro-2-[3-(4-phenyl-1-piperazinyl)propoxy]naphthalene

HRID 2393300노트

반응식

HRID 2393300 반응식
C(O)(C)C.C(O)(=O)C.[N+:9]([C:12]1[C:21]2[CH2:20][CH2:19][CH2:18][CH2:17][C:16]=2[CH:15]=[CH:14][C:13]=1[O:22][CH2:23][CH2:24][CH2:25][N:26]1[CH2:31][CH2:30][N:29]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:28][CH2:27]1)([O-])=O.C(=O)([O-])[O-].[K+].[K+]>O.[Fe].C(OCC)(=O)C>[NH2:9][C:12]1[C:21]2[CH2:20][CH2:19][CH2:18][CH2:17][C:16]=2[CH:15]=[CH:14][C:13]=1[O:22][CH2:23][CH2:24][CH2:25][N:26]1[CH2:31][CH2:30][N:29]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH2:28][CH2:27]1

참가 물질

8

반응물 4

HCID 176Acetic AcidHCID 3776IsopropanolHCID 11430Potassium CarbonateHCID 189755025,6,7,8-Tetrahydro-1-nitro-2-[3-(4-phenyl-1-piperazinyl)propoxy]naphthalene

생성물 1

HCID 189755071-Amino-5,6,7,8-tetrahydro-2-[3-(4-phenyl-1-piperazinyl)propoxy]naphthalene수율 96.4%

시약·촉매·용매 3

HCID 23925Iron촉매HCID 962Water용매2회HCID 8857Ethyl Acetate용매

실험 절차

Iron powder (15 g, 0.27 mol), isopropyl alcohol (45 ml), water (11 ml), and acetic acid (1.5 ml, 26.2 mmol) were added to 5,6,7,8-tetrahydro-1-nitro-2-[3-(4-phenyl-1-piperazinyl)propoxy]naphthalene (5.5g, 13.9 mmol) and stirred for 2 hours under reflux. After cooling the reaction mixture, the mixture was added with potassium carbonate (10 g) that was dissolved in a small volume of water. After stirring for several minutes, ethyl acetate was added to the reaction mixture and the precipitates were removed by filtration. The filtrate was concentrated and the residue was extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous sodium sulfate, and then the solvent was evaporated to give 1-amino-5,6,7,8-tetrahydro-2-[3-(4-phenyl-1-piperazinyl)propoxy]naphthalene (4.9 g).

후처리

  1. temperatureunder reflux
  2. temperatureAfter cooling the reaction mixture
  3. stirringAfter stirring for several minutes
  4. customthe precipitates were removed by filtration
  5. concentrationThe filtrate was concentrated
  6. extractionthe residue was extracted with ethyl acetate
  7. washThe extract was washed with saturated brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. customthe solvent was evaporated

출처 및 근거

ORD 기록
ord-cb14bf041b2c48398dad1f88d507fbef
출처 데이터셋
uspto-grants-1998_09
특허 번호
US05807860

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