Nicotinic Acid → 1-{N-[3-(10,11-Dihydro-5H-dibenz[b,f]-azepin-5-yl)]propyl-N-methylaminocarbonyloxy]ethyl 3-pyridinecarboxylate

HRID 359871Notes

Reaction equation

HRID 359871 reaction equation
[CH:1]1[C:11]2[CH2:10][CH2:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[N:6]([CH2:16][CH2:17][CH2:18][N:19]([CH3:26])[C:20](=[O:25])[O:21][CH:22](Cl)[CH3:23])[C:5]=2[CH:4]=[CH:3][CH:2]=1.[C:27]([OH:35])(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[N:30][CH:29]=1.C(N(CC)CC)C>CN(C)C=O>[N:30]1[CH:31]=[CH:32][CH:33]=[C:28]([C:27]([O:35][CH:22]([O:21][C:20]([N:19]([CH2:18][CH2:17][CH2:16][N:6]2[C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=3[CH2:9][CH2:10][C:11]3[CH:1]=[CH:2][CH:3]=[CH:4][C:5]2=3)[CH3:26])=[O:25])[CH3:23])=[O:34])[CH:29]=1

Participants

5

Reactant 3

HCID 938Nicotinic AcidHCID 8471TriethylamineHCID 156799871-Chloroethyl N-[3-(10,11-dihydro-5H-dibenz[b,f]azepin-5-yl)]propyl-N-methylcarbamate

Product 1

HCID 156799891-{N-[3-(10,11-Dihydro-5H-dibenz[b,f]-azepin-5-yl)]propyl-N-methylaminocarbonyloxy]ethyl 3-pyridinecarboxylateYield 38.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Following the general procedure of Example 52, but using 1.05 g (0.0028 mol) of the product of Example 51, 0.45 g (0.036 mol) of nicotinic acid and 0.36 g of triethylamine in 10 mL dimethylformamide and carrying out the reaction at 25°-30° C. for 48 hours, gave 0.5 g of the title compound as a yellow oil.

Workup

  1. customthe reaction at 25°-30° C. for 48 hours

Sources & evidence

ORD record
ord-49cc95f606e54fdc981d5a54a3d01f9b
Source dataset
uspto-grants-1991_03
Patent number
US05002935

Reaction notes

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