Allylamine → 3-(4-Fluorophenoxy)-N-(2-propenyl)-1-azetidinecarboxamide

HRID 974605

반응식

HRID 974605 반응식
[F:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][CH:7]2[CH2:10][N:9]([C:11](Cl)=[O:12])[CH2:8]2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[NH2:22][CH2:23][CH:24]=[CH2:25]>O1CCCC1.O>[F:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][CH:7]2[CH2:10][N:9]([C:11]([NH:22][CH2:23][CH:24]=[CH2:25])=[O:12])[CH2:8]2)=[CH:4][CH:3]=1

참가 물질

6

반응물 3

HCID 7853AllylamineHCID 11430Potassium CarbonateHCID 150533673-(4-Fluorophenoxy)-1-azetidinecarbonyl chloride

생성물 1

HCID 150534393-(4-Fluorophenoxy)-N-(2-propenyl)-1-azetidinecarboxamide수율 162.6%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

A stirred and cooled (32° C.) mixture of 5.52 g (0.022 mole) of crude 3-(4-fluorophenoxy)-1-azetidine carbonyl chloride and 3 g (0.02 mole) of potassium carbonate in 30 ml of tetrahydrofuran was treated with 1.5 g (0.02 mole) of 3-aminopropylene. The reaction mixture was still exothermic and was stirred for 5 hr as it cooled to ambient temperature. The reaction mixture was diluted with 200 ml of water to produce an oil phase separation. The oil portion was dissolved by extracting with 2×50 ml of benzene. The extracts were combined, dried over magnesium sulfate and concentrated in vacuo to yield 8.14 g of orange-red oil. The oil partially crystallized from benzene-ligroin with charcoal treatment, yielding first a reddish oil followed by a crystalline produce. The total material was concentrated in vacuo to yield 7.45 g of amber-red oil. This oil solidified and was repeatedly triturated with isopropyl ether until only a red oil residue remained. The isopropyl ether portions were repeatedly cooled to the crystallization of residue, decanted from residue and heated to reduce volume until only a straw colored isopropyl ether solution remained. Upon cooling of this solution the title product crystallized and yielded 2.3 g (42.3%) of white crystalline product, m.p. 92°-94° C.

후처리

  1. temperaturecooled
  2. stirringwas stirred for 5 hr as it
  3. customto produce
  4. customan oil phase separation
  5. dissolutionThe oil portion was dissolved
  6. extractionby extracting with 2×50 ml of benzene
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-2468c7f9bbaa46fd96d14072840db15d
출처 데이터셋
uspto-grants-1991_11
특허 번호
US05068231

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