Hydrochloric Acid → HCID 20225046, compound

HRID 1249165Notes

Reaction equation

HRID 1249165 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.Cl.C([NH:19][CH:20]([C:22]1([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[C:28]([Cl:33])[CH:27]=2)[CH2:25][CH2:24][CH2:23]1)[CH3:21])C1C=CC=CC=1.[BH4-].[Na+].Cl>C(O)C.O>[ClH:32].[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([CH2:1][NH:19][CH:20]([C:22]2([C:26]3[CH:31]=[CH:30][C:29]([Cl:32])=[C:28]([Cl:33])[CH:27]=3)[CH2:23][CH2:24][CH2:25]2)[CH3:21])=[CH:3][CH:4]=1

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 312444-MethoxybenzaldehydeHCID 4311764Sodium borohydrideHCID 20225041HCID 20225041, compound

Product 1

HCID 20225046HCID 20225046, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

A stirred mixture of p-anisaldehyde (0.62 ml) and 1-[1-(3,4-dichlorophenyl)cyclobutyl]ethylamine (see Example 1 of published British Patent Specification No. 2098602) in the form of its free base (1.22 g) was heated to 130°-135° for 30 minutes. After cooling the residue was dissolved in ethanol (10 ml) and the solution added to a solution of sodium borohydride (1.5 g) in ethanol (200 ml). The mixture was heated under reflux for one hour. Water (10 ml) and then excess 5N HCl were added and the ethanol removed by evaporation. The residue was basified with aqueous sodium hydroxide solution and an ether extraction performed. The extract was dried and evaporated to give an oil. Hydrogen chloride gas was passed through an ethereal solution of the oil to give N-(4-methoxybenzyl)-1-[1-(3,4-dichlorophenyl)cyclobutyl]ethylamine hydrochloride (m.p. 217°-218° C.).

Workup

  1. temperaturewas heated to 130°-135° for 30 minutes
  2. temperatureAfter cooling the residue
  3. temperatureThe mixture was heated
  4. temperatureunder reflux for one hour
  5. customthe ethanol removed by evaporation
  6. extractionan ether extraction
  7. customThe extract was dried
  8. customevaporated
  9. customto give an oil

Sources & evidence

ORD record
ord-33450d244ff2456695198333430019ce
Source dataset
uspto-grants-1986_12
Patent number
US04629727

Reaction notes

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