Triethylamine → HCID 131717317, compound

HRID 1031184Notes

Reaction equation

HRID 1031184 reaction equation
Cl[CH2:2][CH2:3][CH:4]1[N:17]([CH3:18])[C:9]2=[N:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:8]2[C:7](=[O:19])[N:6]([CH3:20])[CH2:5]1.N1C=CC=CC=1C1CNCCN1.C(N(CC)CC)C.[N:40]1[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=1[N:46]1[CH2:51][CH2:50][NH:49][CH2:48][CH2:47]1>C1(C)C=CC=CC=1>[OH2:19].[CH3:18][N:17]1[C:9]2=[N:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:8]2[C:7](=[O:19])[N:6]([CH3:20])[CH2:5][CH:4]1[CH2:3][CH2:2][N:49]1[CH2:50][CH2:51][N:46]([C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][N:40]=2)[CH2:47][CH2:48]1.[CH3:18][N:17]1[C:9]2=[N:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:8]2[C:7](=[O:19])[N:6]([CH3:20])[CH2:5][CH:4]1[CH2:3][CH2:2][N:49]1[CH2:50][CH2:51][N:46]([C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][N:40]=2)[CH2:47][CH2:48]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 944591-(2-Pyridyl)piperazineHCID 193868302-(Pyridin-2-yl)piperazineHCID 198197592-(2-Chloroethyl)-3,4-dihydro-1,4-dimethyl-1H-[1,3,5]triazepino[3,2-a]benzimidazol-5(2H)-one

Product 1

HCID 131717317HCID 131717317, compoundYield 103.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To 50 mL of toluene was added 5.0 g (0.0171 mol) of 2-(2-chloroethyl)-3,4-dihydro-1,4-dimethyl-1H-[1,3,5]triazepino[3,2-a]benzimidazol-5(2H)-one, 5.58 g (0.034 mol) of 2-(2-pyridyl)piperazine, and 3.4 g (0.034 mol) of triethylamine, and the entire reaction mixture heated to reflux. After 2 days, 1.5 g (0.009 mol) of 1-(2-pyridinyl)piperazine was added and reflux continued for 24 hours. The reaction mixture was washed with 2×50 mL of 1N NaOH, dried over Na2SO4, filtered and concentrated by rotary evaporation. The residue was subjected to preparative HPLC using silica gel as the stationary phase and eluting with 5% triethylamine in acetone. Like fraction were combined affording ~4.0 g (55%) of a glass.

Workup

  1. customthe entire reaction mixture
  2. temperatureheated to reflux
  3. temperaturereflux
  4. waitcontinued for 24 hours
  5. washThe reaction mixture was washed with 2×50 mL of 1N NaOH
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated by rotary evaporation
  9. washeluting with 5% triethylamine in acetone

Sources & evidence

ORD record
ord-26c75822307c4372a136825b8c3718b8
Source dataset
uspto-grants-1992_04
Patent number
US05109013

Reaction notes

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