Hydrochloric Acid → HCID 13279972, compound

HRID 1249174Notes

Reaction equation

HRID 1249174 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([CH:13]([NH2:15])[CH3:14])[CH2:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1.[N:16]1[CH:21]=[CH:20][C:19]([CH:22]=O)=[CH:18][CH:17]=1.[BH4-].[Na+].Cl.[OH-].[Na+]>CO.O>[N:16]1[CH:21]=[CH:20][C:19]([CH2:22][NH:15][CH:13]([C:9]2([C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[CH2:12][CH2:11][CH2:10]2)[CH3:14])=[CH:18][CH:17]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 133894-PyridinecarboxaldehydeHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 20225013HCID 20225013, compound

Product 1

HCID 13279972HCID 13279972, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

1-[1-(4-Methoxyphenyl)cyclobutyl]ethylamine (2.8 g) was heated to 120° C. and 4-pyridinecarboxaldehyde (2.1 g) was added and the mixture was heated at 120°-200° C. for 2 hours. The mixture was allowed to cool and diluted with methanol. Sodium borohydride (1.75 g) was added and the resulting mixture heated under reflux for 21/2 hours. After standing at room temperature for 16 hours the mixture was poured into water, treated with 5N hydrochloric acid and then basified with 5N aqueous sodium hydroxide solution. The product was extracted into ether and the ether extracts were washed with water, dried and evaporated to dryness to give a red oil. The oil was purified by distillation and the distillate dissolved in ether and treated with a solution of excess maleic acid in ether to give a white solid and a sticky yellow gum. Recrystallisation of the white solid from propan-2-ol and ether gave N-(4-pyridylmethyl)-1-[1-(4-methoxyphenyl)cyclobutyl]-ethylamine (1.25) maleate as a pale yellow solid (m.p. 110°-113° C.).

Workup

  1. temperaturethe mixture was heated at 120°-200° C. for 2 hours
  2. temperatureto cool
  3. temperaturethe resulting mixture heated
  4. temperatureunder reflux for 21/2 hours
  5. extractionThe product was extracted into ether
  6. washthe ether extracts were washed with water
  7. customdried
  8. customevaporated to dryness
  9. customto give a red oil
  10. distillationThe oil was purified by distillation
  11. dissolutionthe distillate dissolved in ether
  12. additiontreated with a solution of excess maleic acid in ether
  13. customto give a white solid
  14. customRecrystallisation of the white solid from propan-2-ol and ether

Sources & evidence

ORD record
ord-bf454bbf38fd4855a121d3f1151a0f03
Source dataset
uspto-grants-1986_12
Patent number
US04629727

Reaction notes

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