Acetic Acid → methyl-(6-methyl-1H-indol-3-ylmethyl)-amine

HRID 646075노트

반응식

HRID 646075 반응식
[CH3:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:11]=O)=[CH:7][NH:8]2)=[CH:4][CH:3]=1.C(O)(=O)C.CN.[C:19]([BH3-])#[N:20].[Na+]>CO.O1CCCC1>[CH3:19][NH:20][CH2:11][C:6]1[C:5]2[C:9](=[CH:10][C:2]([CH3:1])=[CH:3][CH:4]=2)[NH:8][CH:7]=1

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 6329MethylamineHCID 47779026-Methylindole-3-carboxaldehydeHCID 5003444Sodium cyanoborohydride

생성물 1

HCID 68579797methyl-(6-methyl-1H-indol-3-ylmethyl)-amine

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

실험 절차

To a suspension of 6-methyl-1H-indole-3-carbaldehyde (0.96 g, Lit. 5) in methanol (15 ml) was added at 22° C. acetic acid (1.7 ml) and a solution of methylamine in tetrahydrofurane (2 M, 12.0 ml). After stirring for 1 h, sodium cyanoborohydride (0.76 g) was added in 5 portions and stirring was continued for 2 h. The mixture was evaporated and the residue partitioned between aqueous hydrochloric acid (1 N) and dichloromethane. The pH of the aqueous layer was adjusted to 14 using sodium hydroxide followed by extraction with dichloromethane. The organic layer was dried and evaporated to give crude methyl-(6-methyl-1H-indol-3-ylmethyl)-amine.

후처리

  1. stirringstirring
  2. waitwas continued for 2 h
  3. customThe mixture was evaporated
  4. customthe residue partitioned between aqueous hydrochloric acid (1 N) and dichloromethane
  5. extractionfollowed by extraction with dichloromethane
  6. customThe organic layer was dried
  7. customevaporated

출처 및 근거

ORD 기록
ord-737666a5d2d94b018f182cb13084127e
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07705034B2

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