Cuminaldehyde → N-(3-ethoxypropyl)-N-(4-isopropylbenzyl)amine

HRID 899888

반응식

HRID 899888 반응식
[CH:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].C(OC)(OC)OC.[CH2:19]([O:21][CH2:22][CH2:23][CH2:24][NH2:25])[CH3:20].[BH4-]>CO.C(Cl)Cl.C(O)(=O)C>[CH2:19]([O:21][CH2:22][CH2:23][CH2:24][NH:25][CH2:8][C:7]1[CH:10]=[CH:11][C:4]([CH:1]([CH3:3])[CH3:2])=[CH:5][CH:6]=1)[CH3:20]

참가 물질

8

반응물 4

HCID 326CuminaldehydeHCID 9005Trimethyl orthoformateHCID 22720Propanolamine ethyl etherHCID 28123Borohydride

생성물 1

HCID 4723366N-(3-ethoxypropyl)-N-(4-isopropylbenzyl)amine수율 83%

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 887Methanol용매HCID 6344Dichloromethane용매

실험 절차

p-iso-Propylbenzaldehyde (1.007 g, 6.798 mmol) was dissolved in methanol (5 ml). Trimethyl orthoformate (5 ml) was added. 3-Ethoxypropylamine (681 mg, 6.6 mmol) was then added and followed by acetic acid (0.2 ml). After standing at room temperature overnight, DCM (5 ml) was added and followed by borohydride on polymer support (5.28 g, 13.2 mmol). The mixture was shaken at room temperature for 4 days and then filtered. The filtrate was evaporated. The residue was dissolved in acetonitrile, then divided into two portions and loaded on 2 columns (ISOLUTE® PRS, 10 g/70 ml, wetted with acetonitrile). It was eluted with acetonitrile, then methanol and then methanol (NH3 sat.). The product fractions were combined and evaporated. Oil product 1.283 g was obtained, yield 83%.

후처리

  1. filtrationfiltered
  2. customThe filtrate was evaporated
  3. dissolutionThe residue was dissolved in acetonitrile
  4. washIt was eluted with acetonitrile
  5. customevaporated

출처 및 근거

ORD 기록
ord-9a66f51ee2ca4707be01d5c6e0b6db42
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07355069B2

연결된 노트

불러오는 중…