2-Pyridinemethanamine → HCID 9909341, compound

HRID 1057608Notes

Reaction equation

HRID 1057608 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(N(C(C)C)CC)(C)C.[NH2:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=1>CN(C=O)C>[CH2:1]([N:8]1[C:20]2[CH:19]=[CH:18][CH:17]=[C:16]([O:21][CH2:22][CH2:23][NH:34][CH2:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=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 195092-PyridinemethanamineHCID 81531DiisopropylethylamineHCID 12044735HCID 12044735, compound

Product 1

HCID 9909341HCID 9909341, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 9-benzyl-4-(2-bromoethoxy)-9H-carbazole (0.0622 g, 0.1635 mmol), diisopropylethylamine (0.0211 g, 0.1635 mmol), 2-(2-aminomethylpyridine (0.0531 g, 0.4907 mmol), and DMF (0.5 mL) is stirred at 100° C. for 30 min. After cooling, the solvent is removed and the residue partitioned between CH2Cl2 and aq. sodium bicarbonate. The organic layers are dried over sodium sulfate; chromatography on silica gel (40 mL) using CH3OH—CH2Cl2 (2/98) gave 0.0539 g (81%) of the title compound; IR (drift) 1586, 1457, 1342, 1269, 1237, 1153, 1145, 1118, 1047, 782, 776, 753, 745, 718, 710 cm−1; 1H NMR (CDClCH3) δ3.32, 4.13, 4.44, 5.51, 6.70, 6.99, 7.12, 7.2-7.4, 7.66, 8.39, 8.60. Anal. Calcd for C27H25N3O: C, 79.58; H, 6.18; N, 10.31. Found: C, 79.66; H, 6.41; N, 10.28.

Workup

  1. temperatureAfter cooling
  2. customthe solvent is removed
  3. customthe residue partitioned between CH2Cl2 and aq. sodium bicarbonate
  4. dry with materialThe organic layers are dried over sodium sulfate

Sources & evidence

ORD record
ord-928d5ceee9744ea5a5631dddabe58e4f
Source dataset
uspto-grants-2003_02
Patent number
US06514968B1

Reaction notes

Loading…