Tacrine → HCID 9819911, compound

HRID 359132Notes

Reaction equation

HRID 359132 reaction equation
[C:1](Cl)(=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].C(N(CC)CC)C.[CH2:20]1[C:33]2[C:24](=[N:25][C:26]3[C:31]([C:32]=2[NH2:34])=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:23][CH2:22][CH2:21]1>C(Cl)(Cl)Cl>[CH2:30]1[C:31]2[C:26](=[N:25][C:24]3[C:33]([C:32]=2[NH:34][C:1](=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH2:27][CH2:28][CH2:29]1

Participants

5

Reactant 3

HCID 1935TacrineHCID 8471TriethylamineHCID 66982Decanoyl chloride

Product 1

HCID 9819911HCID 9819911, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Freshly distilled decanoyl chloride, 5.18 g (0.029 mol), is slowly added to a mixture of 2.94 g (0.029 mol) of triethylamine and 5.82 g (0.029 mol) of 1,2,3,4-tetrahydro-9-acridinamine (Petrow, V., Journal of the Chemical Society, pages 634 to 637 (1947)) in 150 ml of Chloroform. The mixture is heated at reflux for two hours, cooled to room temperature, filtered, and the filtrate evaporated to afford, after repeated washing with diethyl ether, 1.67 g of N-(1,3,4,5-tetrahydro-9-acridinyl)decanamide as a yellow solid: mp 123-126° C.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for two hours
  3. filtrationfiltered
  4. customthe filtrate evaporated
  5. customto afford
  6. washafter repeated washing with diethyl ether, 1.67 g of N-(1,3,4,5-tetrahydro-9-acridinyl)decanamide as a yellow solid

Sources & evidence

ORD record
ord-9de6995e24c34dd4867f3f26ae60d1a3
Source dataset
uspto-grants-1991_03
Patent number
US04999430

Reaction notes

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