Phosphorus oxychloride → 9-Chloro-7-dodecyl-1,2,3,4-tetrahydroacridine

HRID 274868Notes

Reaction equation

HRID 274868 reaction equation
[CH2:1]([C:13]1[CH:26]=[C:25]2[C:16]([N:17]=[C:18]3[C:23](=[C:24]2O)[CH2:22][CH2:21][CH2:20][CH2:19]3)=[CH:15][CH:14]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].O=P(Cl)(Cl)[Cl:30]>>[Cl:30][C:24]1[C:25]2[C:16]([N:17]=[C:18]3[C:23]=1[CH2:22][CH2:21][CH2:20][CH2:19]3)=[CH:15][CH:14]=[C:13]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[CH:26]=2

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178442815HCID 178442815, compound

Product 1

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

Procedure

Three grams of 7-dodecyl-9-hydroxy-1,2,3,4-tetrahydroacridine was refluxed for 30 minutes in 30 mL of POCl3. At the end of this time the POCl3 was evaporated and the residue distributed between aqueous NH3 and ethyl ether. The organic phase was dried and evaporated to give 9-chloro-7-dodecyl-1,2,3,4-tetrahydroacridine (3.0 g) as a solid. A small sample was recrystallized from methanol to give fine needles, mp 36°-38°.

Workup

  1. customAt the end of this time the POCl3 was evaporated
  2. customThe organic phase was dried
  3. customevaporated

Sources & evidence

ORD record
ord-98a53e2b3cc04ca08e646f733569aa39
Source dataset
uspto-grants-1995_02
Patent number
US05391553

Reaction notes

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