Triethylamine → HCID 23194055, compound

HRID 263915Notes

Reaction equation

HRID 263915 reaction equation
Cl[CH:2]1[C:14]2[NH:13][C:12](=[O:15])[C:11](=[O:16])[NH:10][C:9]=2[C:8]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]1=2.[C:17]1([CH:23]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[N:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(N(CC)CC)C>O1CCCC1>[C:30]1([CH:23]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:24]2[CH2:25][CH2:26][N:27]([CH:2]3[C:14]4[NH:13][C:12](=[O:15])[C:11](=[O:16])[NH:10][C:9]=4[C:8]4[CH:7]=[CH:6][CH:5]=[CH:4][C:3]3=4)[CH2:28][CH2:29]2)[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 70048BenzhydrylpiperazineHCID 19035982HCID 19035982, compound

Product 1

HCID 23194055HCID 23194055, compoundYield 23.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

9-Chloro-9H-indeno[1,2-b]pyrazine-2,3(1H, 4H)-dione (1.0 g, 4.26 mmol) was suspended in 10 ml of dry tetrahydrofuran, while cooling in an ice bath. 1-(Diphenylmethyl)piperazine (1.1 g, 4.26 mmol) dissolved in 10 ml of dry tetrahydrofuran was added over 10 min., thereafter triethylamine (0.59 ml, 4.26 mmol) in 3 ml tetrahydrofuran was added. The ice bath was removed and stirring was continued for 20 hours at room temperature. The precipitate was filtered off and washed with tetrahydrofuran to give 1.36 g of the crude product which was recrystallized two times from acetic acid to yield 0.45 g (20%) of the title compound as a hydrochloride. M.p. 212°14 216° C. 1H-NMR (DMSO-d6, δ): 2.5-3.3 (m, 8H), 4.64 (s, 1H), 5.62 (d, 1H), 7.1-7.9 (m, 14H), 11.25 (s, 1H), 11.74 (s, 1H), 12.25 (s, 1H).

Workup

  1. temperaturewhile cooling in an ice bath
  2. additionwas added over 10 min.
  3. customThe ice bath was removed
  4. filtrationThe precipitate was filtered off
  5. washwashed with tetrahydrofuran
  6. customto give 1.36 g of the crude product which
  7. customwas recrystallized two times from acetic acid

Sources & evidence

ORD record
ord-0e5690a71d42481692129a3d93761c21
Source dataset
uspto-grants-1997_07
Patent number
US05646146

Reaction notes

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