Hydrochloric Acid → HCID 20534880, compound

HRID 1156557Notes

Reaction equation

HRID 1156557 reaction equation
C(NCCCCC1C=CC([N+]([O-])=O)=CC=1)CCCCC.C=O.Cl.[CH3:24][N:25]([CH2:32][CH2:33][CH2:34][CH2:35][C:36]1[CH:41]=[CH:40][C:39]([N+:42]([O-:44])=[O:43])=[CH:38][CH:37]=1)[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31].[C:45]([OH:50])(=[O:49])[C:46]([OH:48])=[O:47]>C(OCC)(=O)C.C(O)=O>[C:45]([O-:50])(=[O:49])[C:46]([O-:48])=[O:47].[CH3:24][NH+:25]([CH2:32][CH2:33][CH2:34][CH2:35][C:36]1[CH:37]=[CH:38][C:39]([N+:42]([O-:44])=[O:43])=[CH:40][CH:41]=1)[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31].[CH3:24][NH+:25]([CH2:32][CH2:33][CH2:34][CH2:35][C:36]1[CH:37]=[CH:38][C:39]([N+:42]([O-:44])=[O:43])=[CH:40][CH:41]=1)[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 971Oxalic AcidHCID 12923059HCID 12923059, compoundHCID 12923061HCID 12923061, compound

Product 1

HCID 20534880HCID 20534880, compound

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
95 °C

Procedure

To a cold stirred solution of 2.0 g. of N-n-hexyl-4-(4-nitrophenyl)butylamine in 7 ml. of formic acid were added dropwise 7 ml. of 37% aqueous formaldehyde. The reaction mixture was heated to 95° C. and stirred at this temperature for sixteen hours. The reaction mixture next was cooled and acidified by the addition of 10 ml. of 4 N hydrochloric acid. The aqueous acid mixture was washed twice with diethyl ether, and then made alkaline by the addition of 5 N sodium hydroxide. The product was extracted into diethyl ether. The ethereal extracts were combined, washed with water and dried. Removal of the solvent by evaporation under reduced pressure provided 2.2 g. of N-methyl-N-n-hexyl-4-(4-nitrophenyl)butylamine. The amine was dissolved in ethyl acetate and treated with oxalic acid to give, after crystallization from isopropanol, 2.1 g. of N-methyl-N-n-hexyl-4-(4-nitrophenyl)butylaminium oxalate. M.P. 103°-105° C.

Workup

  1. temperatureThe reaction mixture next was cooled
  2. additionacidified by the addition of 10 ml
  3. washThe aqueous acid mixture was washed twice with diethyl ether
  4. additionby the addition of 5 N sodium hydroxide
  5. extractionThe product was extracted into diethyl ether
  6. washwashed with water
  7. customdried
  8. customRemoval of the solvent
  9. customby evaporation under reduced pressure
  10. customprovided 2.2 g
  11. customto give
  12. customafter crystallization from isopropanol, 2.1 g

Sources & evidence

ORD record
ord-542d2bb7f9284472978eafa549693101
Source dataset
uspto-grants-1982_06
Patent number
US04336269

Reaction notes

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