Acetic Acid → 7-chloro-N-cyclopropyl-2,3-dihydro-1H-inden-1-amine

HRID 2194985노트

반응식

HRID 2194985 반응식
[CH:1]1([NH2:4])[CH2:3][CH2:2]1.C(O)(=O)C.[Cl:9][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:18]=1[C:17](=O)[CH2:16][CH2:15]2.C([BH3-])#N.[Na+]>CO>[Cl:9][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:18]=1[CH:17]([NH:4][CH:1]1[CH2:3][CH2:2]1)[CH2:16][CH2:15]2

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 69828CyclopropylamineHCID 5003444Sodium cyanoborohydrideHCID 112174497-CHLORO-1-INDANONE

생성물 1

HCID 684283077-chloro-N-cyclopropyl-2,3-dihydro-1H-inden-1-amine수율 89.9%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a cooled solution of 4.16 ml (60 mmol) of cyclopropylamine and 4.3 ml (75 mmol) of acetic acid, together with 5 g of 3 Å molecular sieves, in 80 ml of methanol, are added 5 g (30 mmol) of 7-chloro-2,3-dihydro-1H-inden-1-one. The reaction mixture is stirred for 4 hrs at reflux. The reaction mixture is then cooled to ambient temperature and 2.83 g (45 mmol) of sodium cyanoborohydride are slowly added. The reaction mixture is further stirred for 2 hrs at reflux. The solvent is removed under vacuum and 100 ml of water are then added to the residue and the pH is adjusted to 10 with sodium hydroxyde. The watery layer is extracted three times with dichloromethane (3×50 ml); the combined organic layers are dried over magnesium sulphate and concentrated in vacuum to yield 5.6 g (80% yield) of 7-chloro-N-cyclopropyl-2,3-dihydro-1H-inden-1-amine as an brown oil (M+1=208).

후처리

  1. temperatureat reflux
  2. stirringThe reaction mixture is further stirred for 2 hrs
  3. temperatureat reflux
  4. customThe solvent is removed under vacuum and 100 ml of water
  5. additionare then added to the residue
  6. extractionThe watery layer is extracted three times with dichloromethane (3×50 ml)
  7. dry with materialthe combined organic layers are dried over magnesium sulphate
  8. concentrationconcentrated in vacuum

출처 및 근거

ORD 기록
ord-9758f4da96df4d5ca1e3b8b40fb6a742
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08334390B2

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