Acetic Acid → 1-Amino-5,6,7,8-tetrahydro-2-[3-(4-phenyl-1-piperazinyl)propoxy]naphthalene

HRID 2393300Notes

Reaction equation

HRID 2393300 reaction equation
C(O)(C)C.C(O)(=O)C.[N+:9]([C:12]1[C:21]2[CH2:20][CH2:19][CH2:18][CH2:17][C:16]=2[CH:15]=[CH:14][C:13]=1[O:22][CH2:23][CH2:24][CH2:25][N:26]1[CH2:31][CH2:30][N:29]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:28][CH2:27]1)([O-])=O.C(=O)([O-])[O-].[K+].[K+]>O.[Fe].C(OCC)(=O)C>[NH2:9][C:12]1[C:21]2[CH2:20][CH2:19][CH2:18][CH2:17][C:16]=2[CH:15]=[CH:14][C:13]=1[O:22][CH2:23][CH2:24][CH2:25][N:26]1[CH2:31][CH2:30][N:29]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH2:28][CH2:27]1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 3776IsopropanolHCID 11430Potassium CarbonateHCID 189755025,6,7,8-Tetrahydro-1-nitro-2-[3-(4-phenyl-1-piperazinyl)propoxy]naphthalene

Product 1

HCID 189755071-Amino-5,6,7,8-tetrahydro-2-[3-(4-phenyl-1-piperazinyl)propoxy]naphthaleneYield 96.4%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Iron powder (15 g, 0.27 mol), isopropyl alcohol (45 ml), water (11 ml), and acetic acid (1.5 ml, 26.2 mmol) were added to 5,6,7,8-tetrahydro-1-nitro-2-[3-(4-phenyl-1-piperazinyl)propoxy]naphthalene (5.5g, 13.9 mmol) and stirred for 2 hours under reflux. After cooling the reaction mixture, the mixture was added with potassium carbonate (10 g) that was dissolved in a small volume of water. After stirring for several minutes, ethyl acetate was added to the reaction mixture and the precipitates were removed by filtration. The filtrate was concentrated and the residue was extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous sodium sulfate, and then the solvent was evaporated to give 1-amino-5,6,7,8-tetrahydro-2-[3-(4-phenyl-1-piperazinyl)propoxy]naphthalene (4.9 g).

Workup

  1. temperatureunder reflux
  2. temperatureAfter cooling the reaction mixture
  3. stirringAfter stirring for several minutes
  4. customthe precipitates were removed by filtration
  5. concentrationThe filtrate was concentrated
  6. extractionthe residue was extracted with ethyl acetate
  7. washThe extract was washed with saturated brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. customthe solvent was evaporated

Sources & evidence

ORD record
ord-cb14bf041b2c48398dad1f88d507fbef
Source dataset
uspto-grants-1998_09
Patent number
US05807860

Reaction notes

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