Dimethylformamide → HCID 53741928, compound

HRID 361285Notes

Reaction equation

HRID 361285 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.Br[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>C1(C)C=CC=CC=1>[CH2:11]([N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10328IndolineHCID 11430Potassium CarbonateHCID 123691-Bromoheptane

Product 1

HCID 53741928HCID 53741928, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of indoline (17 parts), 1-bromoheptane (31 parts), potassium carbonate (24 parts) and N,N-dimethylformamide (30 parts) was stirred at 100° C. for 3 days. The cooled mixture was diluted with toluene, washed with water (×4), dried (MgSO4) and evaporated to leave 1-heptyl-2,3-dihydro-1H-indole (30 parts).

Workup

  1. washwashed with water (×4)
  2. dry with materialdried (MgSO4)
  3. customevaporated

Sources & evidence

ORD record
ord-e7683a7bca05414b963ccfcfb0ec4f54
Source dataset
uspto-grants-1999_02
Patent number
US05865857

Reaction notes

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