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

HRID 899888ノート

反応式

HRID 899888 の反応式
[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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

実験手順

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%.

後処理

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

出典と根拠

ORDレコード
ord-9a66f51ee2ca4707be01d5c6e0b6db42
出典データセット
uspto-grants-2008_04
特許番号
US07355069B2

反応ノート

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