Triethylamine → HCID 20472398, compound

HRID 2296337Notes

Reaction equation

HRID 2296337 reaction equation
[C:1]([O:4][C:5]1[CH:19]=[CH:18][CH:17]=[CH:16][C:6]=1[C:7]([NH:9][CH:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1)=[O:8])(=[O:3])[CH3:2].Br[CH2:21][CH2:22][CH2:23][O:24][C:25]1[CH:36]=[CH:35][C:28]2[C:29](=[O:34])[CH:30]=[C:31]([CH3:33])[O:32][C:27]=2[CH:26]=1.C(N(CC)CC)C>O1CCCC1>[C:1]([O:4][C:5]1[CH:19]=[CH:18][CH:17]=[CH:16][C:6]=1[C:7]([NH:9][CH:10]1[CH2:15][CH2:14][N:13]([CH2:21][CH2:22][CH2:23][O:24][C:25]2[CH:36]=[CH:35][C:28]3[C:29](=[O:34])[CH:30]=[C:31]([CH3:33])[O:32][C:27]=3[CH:26]=2)[CH2:12][CH2:11]1)=[O:8])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 20472402HCID 20472402, compoundHCID 20472405HCID 20472405, compound

Product 1

HCID 20472398HCID 20472398, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4.9 g. (0.02 mol) 4-(2-acetoxybenzamido)-piperidine, 5.6 g. (0.02 mol) 7-(3-bromopropoxy)-2-methyl-4H-1-benzopyran-4-one, 13.9 ml. (0.10 mol) triethylamine and 100 ml. tetrahydrofuran is heated under reflux for 10 hours and then evaporated. The 7-{3-[4-(2-acetoxybenzamido)-piperidino]-propoxy}-2-methyl-4H-1-benzopyran-4-one obtained as a crude product is mixed with 100 ml. 1 N aqueous sodium hydroxide solution, stirred for 1 hour, filtered, washed with ethyl acetate and the aqueous phase then neutralised. The precipitate obtained is taken up in acetone, mixed with excess ethereal hydrochloric acid and the dihydrochloride of the desired end product isolated; m.p. 169°-170° C. The yield is 4.6 g. (45% of theory).

Workup

  1. additionA mixture of 4.9 g
  2. temperatureunder reflux for 10 hours
  3. customevaporated

Sources & evidence

ORD record
ord-06b4922113644b7298c6df1d2e360d26
Source dataset
uspto-grants-1984_01
Patent number
US04428955

Reaction notes

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