Ammonia → 9-Amino-7-dodecyl-1,2,3,4-tetrahydroacridine, hydrochloride

HRID 274874Notes

Reaction equation

HRID 274874 reaction equation
[Cl:1][C:2]1[C:3]2[C:8]([N:9]=[C:10]3[C:15]=1[CH2:14][CH2:13][CH2:12][CH2:11]3)=[CH:7][CH:6]=[C:5]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH:4]=2.[NH3:28]>>[ClH:1].[NH2:28][C:2]1[C:3]2[C:8]([N:9]=[C:10]3[C:15]=1[CH2:14][CH2:13][CH2:12][CH2:11]3)=[CH:7][CH:6]=[C:5]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH:4]=2

Participants

3

Reactant 2

HCID 222AmmoniaHCID 200889899-Chloro-7-dodecyl-1,2,3,4-tetrahydroacridine

Product 1

HCID 1317188599-Amino-7-dodecyl-1,2,3,4-tetrahydroacridine, hydrochloride

Procedure

A 4.0 g sample of 9-Chloro-7-dodecyl-1,2,3,4-tetrahydroacridine was heated at 150° C. as NH3 was bubbled into the solution. After 2 hours the reaction mixture was distributed between 10% NaOH and 2-butanone and then the organic phase was dried and concentrated. The residue was dissolved in Et2O and treated with 5% HCl. The insoluble hydrochloride was filtered off and recrystallized from MeOH/Et2O to give 2.32 g of analytically pure product, m.p. 257° d.

Workup

  1. customwas bubbled into the solution
  2. customthe organic phase was dried
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in Et2O
  5. additiontreated with 5% HCl
  6. filtrationThe insoluble hydrochloride was filtered off
  7. customrecrystallized from MeOH/Et2O
  8. customto give 2.32 g of analytically pure product, m.p. 257°

Sources & evidence

ORD record
ord-229130cc488a4c9aa299d32b97d66908
Source dataset
uspto-grants-1995_02
Patent number
US05391553

Reaction notes

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