Piperidine, 1-(3-chloropropyl)- → Bis(3-piperidinopropyl) 9-ethylcarbazole-3,6-dicarboxylate dihydrochloride

HRID 441630

Reaction equation

HRID 441630 reaction equation
[CH2:1]([N:3]1[C:15]2[CH:14]=[CH:13][C:12]([C:16]([OH:18])=[O:17])=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[C:7]([C:19]([OH:21])=[O:20])[CH:8]=2)[CH3:2].[N:22]1([CH2:28][CH2:29][CH2:30][Cl:31])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1>[Cl-].C([N+](C)(C)C)C1C=CC=CC=1.C(O)(C)C>[ClH:31].[ClH:31].[N:22]1([CH2:28][CH2:29][CH2:30][O:20][C:19]([C:7]2[CH:6]=[CH:5][C:4]3[N:3]([CH2:1][CH3:2])[C:15]4[C:10]([C:9]=3[CH:8]=2)=[CH:11][C:12]([C:16]([O:18][CH2:30][CH2:29][CH2:28][N:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)=[O:17])=[CH:13][CH:14]=4)=[O:21])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

5

Reactant 2

HCID 79625Piperidine, 1-(3-chloropropyl)-HCID 37979149-ethyl-9H-carbazole-3,6-dicarboxylic acid

Product 1

HCID 21419565Bis(3-piperidinopropyl) 9-ethylcarbazole-3,6-dicarboxylate dihydrochloride

Reagents, catalysts & solvents 2

HCID 5963Benzyltrimethylammonium chlorideCatalystHCID 3776IsopropanolSolvent

Procedure

To 250 ml of isopropyl alcohol is added one equivalent of 9-ethylcarbazole-3,6-dicarboxylic acid, 2 equivalents of 3-piperidinopropylchloride, and a catalytic amount of benzyltrimethylammonium chloride. The mixture is heated to reflux for 2 hours. Upon cooling a solid forms which is collected, washed with ether, dried and dissolved in water. The aqueous solution is made basic with saturated sodium bicarbonate, and the product is extracted with ether. The ether solution is washed with water, dried, and acidified with ethereal HCl. The resulting precipitate is recrystallized from methanol-butanone to give bis(3-piperidinopropyl)-9-ethylcarbazole-3,6-dicarboxylate dihydrochloride.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux for 2 hours
  3. temperatureUpon cooling a solid forms which
  4. customis collected
  5. washwashed with ether
  6. customdried
  7. dissolutiondissolved in water
  8. extractionthe product is extracted with ether
  9. washThe ether solution is washed with water
  10. customdried
  11. customThe resulting precipitate is recrystallized from methanol-butanone

Sources & evidence

ORD record
ord-911df8559773457783bef87d2651d22c
Source dataset
uspto-grants-1977_08
Patent number
US04041165

Linked notes

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