Triethylamine → HCID 12967333, compound

HRID 1057616Notes

Reaction equation

HRID 1057616 reaction equation
[CH2:1]([N:8]1[C:20]2[CH:19]=[CH:18][CH:17]=[C:16]([O:21][CH2:22][CH2:23]Br)[C:15]=2[C:14]2[C:9]1=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:25]([N:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1)([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26].C(N(CC)CC)C>C(#N)C>[CH2:1]([N:8]1[C:20]2[CH:19]=[CH:18][CH:17]=[C:16]([O:21][CH2:22][CH2:23][N:35]3[CH2:34][CH2:33][N:32]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:37][CH2:36]3)[C:15]=2[C:14]2[C:9]1=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 12044735HCID 12044735, compound

Product 1

HCID 12967333HCID 12967333, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 9-benzyl-4-(2-bromoethoxy)-9H-carbazole (0.0647 g, 0.170 mmol), Boc-piperazine (0.0380 g, 0.204 mmol), triethylamine (0.0206 g, 0.204 mmol), and acetonitrile (2 mL) is heated at reflux for 24 h. After cooling, the mixture is partitioned between CH2Cl2 and aq. sodium bicarbonate. The organic layers are dried over sodium sulfate; chromatography on silica gel eluting with CH3OH—CH2Cl2 (2/98) gave poor separation of product and impurities. Re-chromatography (silica gel, 20 mL) using acetone-hexane (10/90 to 20/80) gave 0.0650 g (83%) of the title compound; IR (drift) 1693, 1457, 1420, 1365, 1341, 1332, 1291, 1266, 1243, 1174, 1154, 1145, 1129, 1112, 752 cm−1; 1H NMR (CDCl3) δ1.46, 2.65, 3.06, 3.48, 4.41, 5.51, 6.69, 6.99, 7.12, 7.2-7.4, 8.37. Anal. Calcd for C30H35N3O3: C, 74.20; H, 7.26; N, 8.65. Found: C, 73.82; H, 7.41; N, 8.52.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 24 h
  3. temperatureAfter cooling
  4. customthe mixture is partitioned between CH2Cl2 and aq. sodium bicarbonate
  5. dry with materialThe organic layers are dried over sodium sulfate
  6. customchromatography on silica gel eluting with CH3OH—CH2Cl2 (2/98) gave poor
  7. customseparation of product and impurities

Sources & evidence

ORD record
ord-1815fa05ad144e50b01f89498ae035e7
Source dataset
uspto-grants-2003_02
Patent number
US06514968B1

Reaction notes

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