Dipropylamine → HCID 21842221, compound

HRID 1418930Notes

Reaction equation

HRID 1418930 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-methyl-5,6-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-0f3484c3e42941e49413e0a790c194a5
Source dataset
uspto-grants-1999_03
Patent number
US05885986

Reaction notes

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