Cyclopropylamine → N-(3,3-bis(4-fluorophenyl)propyl)cyclopropanamine

HRID 2190350노트

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HRID 2190350 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[CH2:9][CH:10]=O)=[CH:4][CH:3]=1.[CH:19]1([NH2:22])[CH2:21][CH2:20]1.[BH4-].[Na+]>CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[CH2:9][CH2:10][NH:22][CH:19]2[CH2:21][CH2:20]2)=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 69828CyclopropylamineHCID 4311764Sodium borohydrideHCID 183626473,3-Bis(4-fluorophenyl)propanal

생성물 1

HCID 57586327N-(3,3-bis(4-fluorophenyl)propyl)cyclopropanamine

시약·촉매·용매 1

HCID 887Methanol용매

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온도
25 °C

실험 절차

To solution of 3,3-bis(4-fluorophenyl)propanal (1.00 g, 4.06 mmol, see Method H for preparation) in MeOH (15 ml) was added cyclopropanamine (0.285 ml, 4.06 mmol). The reaction mixture was stirred for overnight at 25° C. Sodium borohydride (0.307 g, 8.12 mmol) was carefully added to the reaction mixture over 15 min. After stirring an additional 15 min volatiles were removed by concentration under reduced pressure. The leftover residue was solubilized with 60 mL of a 1:2 mixture of 10% NaOH and ethyl acetate. The organic phase was separated and the aqueous phase was extracted further with ethyl acetate (2×40 mL). Purification by chromatography on silica (eluted with 0->10% MeOH/CH2Cl2+0->1% NH4OH) gave N-(3,3-bis(4-fluorophenyl)propyl)cyclopropanamine 181. The product was dissolved in CH2Cl2 and made into the HCl salt by precipitation with etheral HCl and then concentration of volatiles.

후처리

  1. stirringAfter stirring an additional 15 min volatiles
  2. customwere removed by concentration under reduced pressure
  3. additionThe leftover residue was solubilized with 60 mL of a 1:2 mixture of 10% NaOH and ethyl acetate
  4. customThe organic phase was separated
  5. extractionthe aqueous phase was extracted further with ethyl acetate (2×40 mL)
  6. customPurification by chromatography on silica (eluted with 0->10% MeOH/CH2Cl2+0->1% NH4OH)

출처 및 근거

ORD 기록
ord-6c5cd7f7ce3642f7be43918c7b506a45
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08324396B2

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