Hydrochloric Acid → 4-(4-Methoxyphenyl)butan-1-amine hydrochloride

HRID 352063노트

반응식

HRID 352063 반응식
FC(F)(F)S(O)(=O)=O.[NH2:9][CH2:10][CH2:11][CH2:12][C:13]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)=O.CC(O)C.[ClH:27]>C1(CCCCN2N=CC=N2)C=CC=CC=1.[C].[Pd]>[ClH:27].[NH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:15]1[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=1

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 3776Isopropanol2회HCID 227150434-Amino-4'-methoxybutyrophenone trifluoromethanesulfonate

생성물 1

HCID 227150474-(4-Methoxyphenyl)butan-1-amine hydrochloride수율 85%

시약·촉매·용매 2

HCID 178418390HCID 178418390, 화합물촉매HCID 129928422-(4-Phenylbutyl)-2h-1,2,3-triazole용매

실험 절차

4-Amino-4′-methoxybutyrophenone trifluoromethanesulfonate (60 g, 174.8 mmol) was dissolved in tetrahydrofuran/water-1/1 (600 ml) and 10% palladium carbon (water-containing product, 6 g) was added. The mixture was subjected to catalytic reduction at 50° C. for 7 hours under hydrogen pressure (0.8 Mpa). The catalyst was filtered off and toluene (360 ml) and 2N-potassium hydroxide (180 ml) were added. The mixture was partitioned and the aqueous layer was extracted with toluene (360 ml). The organic layers were combined and washed with 20% brine (3 times). To the residue obtained by concentration under reduced pressure was added 2-propanol (300 ml) and con. hydrochloric acid (34 ml) was added dropwise under ice-cooling. To the residue obtained by concentration under reduced pressure was added 2-propanol (300 ml) and the mixture was concentrated under reduced pressure. 2-Propanol (300 ml) was added and the mixture was concentrated under reduced pressure. To the obtained residue was added isopropyl ether (200 ml) and the mixture was stirred at room temperature for 10 min. The precipitated crystals were collected by filtration and dried under reduced pressure to give 1-(4-aminobutyl)-4-methoxybenzene hydrochloride (32.1 g, yield 85%).

후처리

  1. filtrationThe catalyst was filtered off
  2. additiontoluene (360 ml) and 2N-potassium hydroxide (180 ml) were added
  3. customThe mixture was partitioned
  4. extractionthe aqueous layer was extracted with toluene (360 ml)
  5. washwashed with 20% brine (3 times)
  6. customTo the residue obtained by concentration under reduced pressure
  7. temperaturecooling
  8. customTo the residue obtained by concentration under reduced pressure
  9. concentrationthe mixture was concentrated under reduced pressure
  10. addition2-Propanol (300 ml) was added
  11. concentrationthe mixture was concentrated under reduced pressure
  12. additionTo the obtained residue was added isopropyl ether (200 ml)
  13. filtrationThe precipitated crystals were collected by filtration
  14. customdried under reduced pressure

출처 및 근거

ORD 기록
ord-f46db01d1d194e519f340ed0329812d8
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06743924B2

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