Dimethylformamide → HCID 69514914, compound

HRID 49494Notes

Reaction equation

HRID 49494 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH2:18][CH:19]=[CH:20][CH2:21]Br)=[CH:14][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:23]([CH2:26][NH2:27])[CH:24]=C.[CH3:28]N(C=O)C>>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH2:18][CH:19]=[CH:20][CH2:21][N:27]([CH2:26][CH:23]=[CH2:24])[CH3:28])=[CH:14][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 4437323-Buten-1-amineHCID 695150785-(4-Bromo-but-2-enyloxy)-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester

Product 1

HCID 69514914HCID 69514914, compoundYield 83%

Procedure

214 mg (0.6 mmol) 5-(4-Bromo-but-2-enyloxy)-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester in 3 ml DMF were treated with 213 mg (3 mmol) N-allylmethylamine at 50° C. for 0.5 h. The mixture was extracted with ether and water. The organic phase was washed with water and dried over Na2SO4 and evaporated to yield 180 mg (83%) 5-[4-(Allyl-methyl-amino)-but-2-enyloxy]-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester as yellow oil, MS: 359 (MH+).

Workup

  1. extractionThe mixture was extracted with ether and water
  2. washThe organic phase was washed with water
  3. dry with materialdried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-73ef3105732044a7a688f09e6434ffc8
Source dataset
uspto-grants-2004_03
Patent number
US06706751B2

Reaction notes

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