1,3-Dibromopropane → HCID 18599317, 화합물

HRID 1906425노트

반응식

HRID 1906425 반응식
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[C:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]2[NH2:15])=[CH:4][CH:3]=1.Br[CH2:17][CH2:18][CH2:19]Br.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[CH3:1][C:2]1[CH:3]=[CH:4][C:5](/[CH:8]=[C:9]2/[CH:10]([N:15]3[CH2:19][CH2:18][CH2:17]3)[CH2:11][CH2:12][CH2:13][CH2:14]/2)=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 53709014HCID 53709014, 화합물2회

생성물 1

HCID 18599317HCID 18599317, 화합물

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A mixture of N-[2-[(4-methylphenyl)methylene]cyclohexyl]amine, from step C above, 0.64 g (3.2 mmol) with 1.28 g (6.4 mmol) of 1,3-dibromopropane and 0.88 g (6.4 mmol) of potassium carbonate in 20 ml of ethanol was refluxed 18 hr, evaporated and the residue was taken up in a water/diethyl ether mixture. The aqueous layer was separated and saturated with solid potassium hydroxide and extracted with diethyl ether. The ether extract was washed with saturated sodium chloride solution, dried with magnesium sulfate and evaporated. The residue, 0.67 g, was chromatographed using a HPLC Merck C silica gel column using a 3% methanol in chloroform solution containing 0.5% ammonium hydroxide mixture as eluent. Elution with 620 ml of this eluting mixture gave mixtures of products containing the N-allyl derivative of the starting N-[2-[(4-methylphenyl)methylene]cyclohexyl]amine. Elution of the column contents with 5% methanol in chloroform containing 0.5% ammonium hydroxide (240 ml) gave no product. The next 540 ml gave 180 mg of (±)-(E)-1-[2-[(4-methylphenyl)methylene]cyclohexyl]-azetidine. GC analyses (3% SE 30) 100% at 4.99 min, UV λmax(ε)247(15,300). HR mass spectrum Found 241.1844, Calcd. for C17H23N 241.1830. The NMR spectrum was also consistent for this named product.

후처리

  1. customevaporated
  2. customThe aqueous layer was separated and saturated with solid potassium hydroxide
  3. extractionextracted with diethyl ether
  4. extractionThe ether extract
  5. washwas washed with saturated sodium chloride solution
  6. dry with materialdried with magnesium sulfate
  7. customevaporated
  8. customThe residue, 0.67 g, was chromatographed
  9. additioncontaining 0.5% ammonium hydroxide mixture as eluent
  10. washElution with 620 ml of this eluting mixture
  11. customgave mixtures of products
  12. washElution of the column contents with 5% methanol in chloroform containing 0.5% ammonium hydroxide (240 ml)
  13. customgave no product

출처 및 근거

ORD 기록
ord-ee0ee5a195d646f0b8410c61fb4ed755
출처 데이터셋
uspto-grants-1987_03
특허 번호
US04652559

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