Sodium borohydride → HCID 178418401, Verbindung

HRID 1737927

Reaktionsgleichung

Reaktionsgleichung von HRID 1737927
[CH3:1][N:2]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[CH2:16][CH2:15][C:14](=[O:17])[CH2:13][CH2:12]2)=[CH:7][CH:6]=1)[CH3:3].[BH4-].[Na+]>CO>[CH3:3][N:2]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C@H:11]2[CH2:16][CH2:15][C@H:14]([OH:17])[CH2:13][CH2:12]2)=[CH:7][CH:6]=1)[CH3:1]

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 153795844-{4-[(Dimethylamino)methyl]phenyl}cyclohexan-1-one

Produkt 1

HCID 178418401HCID 178418401, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 11.1 g (0.048 mol) of 4-(4-dimethylaminomethylphenyl)-cyclohexanone in 100 ml of absolute methanol, which has been cooled to -10° C., is added 1.82 g (0.048 mol) of sodium borohydride in batches with stirring. The reaction mixture is allowed to react for 1.5 hours at ambient temperature and then evaporated down in vacuo. The residue remaining is mixed with water, acidified with concentrated hydrochloric acid, stirred for 30 minutes at ambient temperature, made alkaline with 50 sodium hydroxide solution and extracted several times with chloroform. The combined extracts are dried with sodium sulphate and evaporated down in vacuo. The residue remaining, which consists of a mixture of trans/cis-4-(4-dimethylaminomethylphenyl)-cyclohexanol (cis fraction <10%) is purified by column chromatography (aluminium oxide neutral, activity stage III, ICN; petroleum ether/methylethyl ketone=5:1). White crystals are obtained, melting point 63-65° C. Yield: 8.8 g (79% of theory), C15H23NO (233.36) Calculated: C 77.21 H 9.93 N 6.00 Found: 77.34 10.02 5.89

Aufarbeitung

  1. customto react for 1.5 hours at ambient temperature
  2. customevaporated down in vacuo
  3. additionThe residue remaining is mixed with water
  4. stirringstirred for 30 minutes at ambient temperature
  5. extractionextracted several times with chloroform
  6. dry with materialThe combined extracts are dried with sodium sulphate
  7. customevaporated down in vacuo
  8. additionwhich consists of a mixture of trans/cis-4-(4-dimethylaminomethylphenyl)-cyclohexanol (cis fraction <10%)
  9. customis purified by column chromatography (aluminium oxide neutral, activity stage III, ICN; petroleum ether/methylethyl ketone=5:1)
  10. customWhite crystals are obtained

Quellen und Nachweise

ORD-Eintrag
ord-ef2874fdde094aa48ec43675534e8777
Quelldatensatz
uspto-grants-1999_10
Patentnummer
US05962507

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