Diisopropylamine → HCID 67315799, compound

HRID 1012584Notes

Reaction equation

HRID 1012584 reaction equation
C(N(CCC)[CH2:5][CH2:6][CH2:7][CH2:8][CH:9]([NH2:25])[C:10]1[CH:15]=[CH:14][C:13]([CH2:16][N:17]=[CH:18][C:19]2[O:20][C:21]([CH3:24])=[CH:22][CH:23]=2)=[CH:12][CH:11]=1)CC.C[N:30]1[CH2:34][CH2:33][CH2:32][C:31]1=O.[CH:36](NC(C)C)(C)[CH3:37].[CH2:43](Br)[CH2:44][CH2:45][CH2:46][CH2:47][CH3:48]>O>[CH2:34]([N:30]([CH2:31][CH2:36][CH3:37])[CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]([NH2:25])[C:10]1[CH:11]=[CH:12][C:13]([CH2:16][N:17]=[CH:18][C:19]2[O:20][C:21]([CH3:24])=[CH:22][CH:23]=2)=[CH:14][CH:15]=1)[CH2:33][CH3:32]

Participants

6

Reactant 4

HCID 7912DiisopropylamineHCID 81011-BromohexaneHCID 13387N-methyl-2-pyrrolidoneHCID 67315765HCID 67315765, compound

Product 1

HCID 67315799HCID 67315799, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under a nitrogen stream 488 mg (1.27 mmol, 1.0 equivalent) of {(4-dipropylaminobutyl)-[4-(5-methylfuran-2-ylmethylidene)aminomethylbenzyl]}amine (26), 8 ml of N-methyl-2-pyrrolidinone, 193 mg (1.91 mmol, 1.5 equivalents) of diisopropylamine, and 252 mg (1.53 mmol, 1.2 equivalents) of 1-hexyl bromide were charged in a 50 ml recovery flask and reacted at 26° C. for six days. The reaction solution was added with 30 ml of water, and extracted with 50 ml of toluene. The organic layer was washed three times with 20 ml of a saturated sodium bicarbonate aqueous solution, washed with 20 ml of water, dried over anhydrous sodium sulfate, and concentrated, thereby obtaining 443 mg of {(4-dipropylaminobutyl)-n-hexyl-[4-(5-methylfuran-2-ylmethylidene)aminomethylbenzyl]}amine (35) as a reddish brown oily substance (yield: 85%).

Workup

  1. customreacted at 26° C. for six days
  2. extractionextracted with 50 ml of toluene
  3. washThe organic layer was washed three times with 20 ml of a saturated sodium bicarbonate aqueous solution
  4. washwashed with 20 ml of water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f5b68b70e4fe403f87ad88a89bb1f25b
Source dataset
uspto-grants-2011_07
Patent number
US07977512B2

Reaction notes

Loading…