Dipropylamine → HCID 21842221, compound

HRID 1737346Notes

Reaction equation

HRID 1737346 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]([C:8]2[N:9]=[CH:10][N:11]3[C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=4[C:15](=[O:22])[N:14]([CH3:23])[CH2:13][C:12]=23)[S:6][CH:7]=1.[CH2:24]([NH:27][CH2:28][CH2:29][CH3:30])[CH2:25][CH3:26]>O1CCCC1>[CH2:24]([N:27]([CH2:2][C:3]1[N:4]=[C:5]([C:8]2[N:9]=[CH:10][N:11]3[C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=4[C:15](=[O:22])[N:14]([CH3:23])[CH2:13][C:12]=23)[S:6][CH:7]=1)[CH2:28][CH2:29][CH3:30])[CH2:25][CH3:26]

Participants

4

Reactant 2

HCID 8902DipropylamineHCID 21842289HCID 21842289, compound

Product 1

HCID 21842221HCID 21842221, compoundYield 56.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1.0 g (0.0029 mol) of 3-(4-chloromethyl-thiazol-2-yl)-5-methyl-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one in 60 ml of tetrahydrofuran was treated with 7.9 ml (0.058 mol) of dipropylamine. After stirring at reflux for 16 hrs. the solution obtained was completely freed from the solvents. The residue was chromatographed over silica gel with ethyl acetate and the eluent and recrystallized from hot isopropyl ether. There was obtained 0.67 g (56%) of 3-(4-dipropylaminomethyl-thiazol-2-yl)-5-methyl5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one as white crystals; m.p. 111-112°.

Workup

  1. temperatureat reflux for 16 hrs
  2. customthe solution obtained
  3. customThe residue was chromatographed over silica gel with ethyl acetate
  4. customthe eluent and recrystallized from hot isopropyl ether

Sources & evidence

ORD record
ord-efd7a444c77d44cca374f2059457ecd3
Source dataset
uspto-grants-1999_10
Patent number
US05962450

Reaction notes

Loading…