Sodium Hydroxide → HCID 54570919, compound

HRID 1719522Notes

Reaction equation

HRID 1719522 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][NH:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH:7]1[CH:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)O.[OH-].[Na+]>Cl>[OH:1][CH2:2][CH2:3][CH2:4][NH:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][C:7]1=[CH:12][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 13504835HCID 13504835, compound

Product 1

HCID 54570919HCID 54570919, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of N-(3-hydroxypropyl)-N-[2-[phenyl(hydroxy)methyl]cyclohexyl]amine, from step (a) above, 50 g (0.19 mole) and 250 ml of concentrated hydrochloric acid was heated on a steam bath for 1.5 hr. The resulting solution was cooled in ice, basified with 20% aqueous sodium hydroxide solution and the product was extracted well with diethyl ether. The ether extract was dried with magnesium sulfate and evaporated to give 45.3 g of N-(3-hydroxypropyl)-N-[2-(phenylmethylene)cyclohexyl]amine, as an oil, which was used directly in the next preparative step. However, a portion of this amine oil was converted to its hydrochloride in methanol with a diethyl ether solution of hydrogen chloride and the salt was crystallized from the methanol/diethyl ether mixture, mp 175°-177° C. The IR, UV and NMR spectra were consistent.

Workup

  1. temperatureThe resulting solution was cooled in ice
  2. extractionthe product was extracted well with diethyl ether
  3. extractionThe ether extract
  4. dry with materialwas dried with magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-6c9d4bd4500646c7a3b7dce7b0f118a6
Source dataset
uspto-grants-1985_09
Patent number
US04540690

Reaction notes

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