Hydrochloric Acid → HCID 68869253, compound

HRID 1391400Notes

Reaction equation

HRID 1391400 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][CH2:14][NH:15][C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][CH:17]=1.[ClH:25]>CO>[ClH:25].[NH2:1][CH2:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][CH2:14][NH:15][C:16]1[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 56652140N-(3-{2-[2-(3-aminopropoxy)ethoxy]ethoxy}propyl)-N-(4-nitrophenyl)amine

Product 1

HCID 68869253HCID 68869253, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

1.5 g of nitro derivative (19) prepared above and about 100 ml of methanol were introduced into a 200 ml autoclave (hydrogenator) equipped with a magnetic stirrer. The solution obtained was degassed with nitrogen. 0.4 g of palladium-on-charcoal (5% humidity, comprising 50% water) was added thereto. The reaction mixture was stirred, while flushing once with hydrogen, and hydrogen was then introduced to a pressure of about 5 bar. After reaction for 4 hours, the reactor was flushed with nitrogen and the reaction mixture was filtered quickly through Celite under a gentle pressure of nitrogen. The filtrate was recovered in a pre-cooled solution of methanol comprising about 3 equivalents of hydrogen chloride gas. It was rinsed several times with methanol under a stream of nitrogen. The solution thus obtained was concentrated and was then treated with ether. The product obtained, in the form of a pale pink paste, was stirred and then rinsed several times with acetonitrile and ether under nitrogen. 1.6 g of expected product (20) were isolated in the form of a slightly pink white powder.

Workup

  1. additionwere introduced into a 200 ml autoclave (hydrogenator)
  2. customequipped with a magnetic stirrer
  3. customThe solution obtained
  4. customwas degassed with nitrogen
  5. addition0.4 g of palladium-on-charcoal (5% humidity, comprising 50% water) was added
  6. customwhile flushing once with hydrogen, and hydrogen
  7. additionwas then introduced to a pressure of about 5 bar
  8. customAfter reaction for 4 hours
  9. customthe reactor was flushed with nitrogen
  10. filtrationthe reaction mixture was filtered quickly through Celite under a gentle pressure of nitrogen
  11. washIt was rinsed several times with methanol under a stream of nitrogen
  12. customThe solution thus obtained
  13. concentrationwas concentrated
  14. additionwas then treated with ether
  15. customThe product obtained, in the form of a pale pink paste
  16. stirringwas stirred
  17. washrinsed several times with acetonitrile and ether under nitrogen

Sources & evidence

ORD record
ord-95b1db49607c45b6855850787277c0e3
Source dataset
uspto-grants-2008_03
Patent number
US07338536B2

Reaction notes

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