Pyrrolidine → HCID 9842349, compound

HRID 1057615Notes

Reaction equation

HRID 1057615 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.[NH:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1>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:25]3[CH2:29][CH2:28][CH2:27][CH2:26]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

4

Reactant 2

HCID 31268PyrrolidineHCID 12044735HCID 12044735, compound

Product 1

HCID 9842349HCID 9842349, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 9-benzyl-4-(2-bromoethoxy)-9H-carbazole (0.020 g, 0.0526 mmol), pyrrolidine (0.040 g, 0.562 mmol), and acetonitrile (1.0 mL) is stirred over the weekend at room temperature; much starting material remained so the mixture is heated at 75° C. in a capped vial for 24 h. After cooling and removal of the solvent, the residue is partitioned between CH2Cl2 and aq. sodium bicarbonate. The organic layers are dried over sodium sulfate; chromatography on silica gel eluting with CH3OH—CH2Cl2 (4/96) gave 0.0165 g (85%) of the title compound as a waxy solid; 1H NMR (CDCl3) δ1.97, 3.04, 3.36, 4.59, 5.30, 6.71, 7.02, 7.12, 7.2-7.4, 8.32. Anal. Calcd for C25H26N2O: C, 81.05; H, 7.07; N, 7.56. Found: C, 79.84; H, 7.02; N, 7.44.

Workup

  1. temperatureis heated at 75° C. in a capped vial for 24 h
  2. temperatureAfter cooling
  3. customremoval of the solvent
  4. customthe residue is partitioned between CH2Cl2 and aq. sodium bicarbonate
  5. dry with materialThe organic layers are dried over sodium sulfate

Sources & evidence

ORD record
ord-76c601c2e9084f3fbb65fdfb03254a04
Source dataset
uspto-grants-2003_02
Patent number
US06514968B1

Reaction notes

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