Water → HCID 15728406, compound

HRID 359133Notes

Reaction equation

HRID 359133 reaction equation
C([Li])CCC.[CH2:6]1[C:19]2[C:10](=[N:11][C:12]3[C:17]([C:18]=2[NH2:20])=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH2:9][CH2:8][CH2:7]1.Cl[C:22]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[O:23].O>O1CCCC1>[CH2:16]1[C:17]2[C:12](=[N:11][C:10]3[C:19]([C:18]=2[NH:20][C:22](=[O:23])[O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH2:13][CH2:14][CH2:15]1

Participants

6

Reactant 4

HCID 962WaterHCID 1935TacrineHCID 81956Carbonochloridic acid, octyl esterHCID 178418339Butyllithium

Product 1

HCID 15728406HCID 15728406, compoundYield 56.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

n Butyllithium, 0.033 mol, is added to a suspension of 6.5g (0.033 mol) of 1,2,3,4-tetra -hydro-9-acridinamine (Petrow, V., Journal of the Chemical Society, pages 634 to 637 (1947)) in 200 ml of tetrahydrofuran at 0° C. The mixture is stirred at 0° C. for 20 minutes, the cooling bath removed and 6.36 g (0.033 mol) of octyl chloroformate added and the solution stirred over the weekend. Water, 200 ml, is added and the mixture extracted with ethyl acetate. The ethyl acetate layer is separated and evaporated to afford a yellow oil. Chromatography (elution with isopropanol-chloroform (5:95)) affords 6.59 g of octyl (1,2,3,4-tetrahydro-9-acridinyl)carbamate, as a yelIow solid; mp 96-99° C.

Workup

  1. customat 0° C
  2. customthe cooling bath removed
  3. stirringthe solution stirred over the weekend
  4. extractionthe mixture extracted with ethyl acetate
  5. customThe ethyl acetate layer is separated
  6. customevaporated
  7. customto afford a yellow oil
  8. washChromatography (elution with isopropanol-chloroform (5:95))

Sources & evidence

ORD record
ord-0c90483b49aa40d7b98845a1cb70c60f
Source dataset
uspto-grants-1991_03
Patent number
US04999430

Reaction notes

Loading…