Dibutylamine → HCID 10111190, compound

HRID 2296738Notes

Reaction equation

HRID 2296738 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:13]=[C:14]3[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][N:15]3[CH:21]=2)=[CH:8][CH:7]=1.[CH2:22]([NH:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH2:23][CH2:24][CH3:25]>>[CH2:22]([N:26]([CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:13]=[C:14]3[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][N:15]3[CH:21]=2)=[CH:8][CH:7]=1)[CH2:27][CH2:28][CH2:29][CH3:30])[CH2:23][CH2:24][CH3:25]

Participants

3

Reactant 2

HCID 8148DibutylamineHCID 14201487HCID 14201487, compound

Product 1

HCID 10111190HCID 10111190, compound

Procedure

The product of Step C (8.6 g) and dibutylamine (9 mL) were heated at reflux temperature for 8 hours. The reaction was cooled to ambient temperature and evaporated in vacuo. The residue was purified via silica gel chromatography (dichloromethane/acetone) to give the title compound which was converted to a hydrochloride salt upon addition of concentrated hydrochloric acid. The salt was recrystallized (methanol/acetone/ether) to give 5.66 g of product. (m.p. 188-191° C).

Workup

  1. temperatureat reflux temperature for 8 hours
  2. customevaporated in vacuo
  3. customThe residue was purified via silica gel chromatography (dichloromethane/acetone)

Sources & evidence

ORD record
ord-8a46002aadbb400795ccc5a6bcbbe2b9
Source dataset
uspto-grants-2002_12
Patent number
US06489337B1

Reaction notes

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