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

HRID 646075Notes

Reaction equation

HRID 646075 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-737666a5d2d94b018f182cb13084127e
Source dataset
uspto-grants-2010_04
Patent number
US07705034B2

Reaction notes

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