Hydrochloric Acid → 2-Iodo-5-methoxy-N,alphadimethylbenzenepropanamine Hydrochloride

HRID 543429Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 543429
CN.[I:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:5]=1[CH2:12][CH2:13][C:14](=O)[CH3:15].[C:17]([BH3-])#[N:18].[Na+].[ClH:21].CN.Cl>CO.CCOCC>[ClH:21].[I:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:5]=1[CH2:12][CH2:13][CH:14]([CH3:15])[NH:18][CH3:17]

Komponenten

8

Edukt 5

HCID 313Hydrochloric Acid2×HCID 6329MethylamineHCID 5003444Sodium cyanoborohydrideHCID 6364545Methylamine hydrochlorideHCID 140254744-(2-Iodo-5-methoxyphenyl)butan-2-one

Produkt 1

HCID 139107782-Iodo-5-methoxy-N,alphadimethylbenzenepropanamine HydrochlorideAusbeute 55,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittel2×HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

A solution of 19.41 g (0.625 mole) of methylamine in 400 ml of anhydrous methanol was treated with 37.92 g (0.125 mole) of 4-(2-iodo-5-methoxyphenyl)-2-butanone, 6.28 g (0.1 mole) of sodium cyanoborohydride and 21.07 g (0.312 mole) of methylamine hydrochloride and allowed to stir at room temperature under an atmosphere of nitrogen for 21/2 hours. The resulting mixture was cooled in an ice bath and treated with concentrated hydrochloric acid to pH 1. The solvent was evaporated in vacuo and the residue partitioned between 1.5 l of water and 600 ml of ether. The water layer was separated and treated with 50% sodium hydroxide solution until basic. The resulting crude product was extracted into 500 ml of ether, washed with brine, and the brine layer extracted with an additional 400 ml portion of ether. The combined ether layers were dried over anhydrous potassium carbonate and evaporated in vacuo to yield 31.09 g (78%) of crude oil. The oil was dissolved in methanol and treated with ethereal hydrogen chloride until neutral. Ether was added to the mixture and the resulting hydrochloride salt separated by filtration to give 19.75 g (44%) of crude product. One recrystallization from 2-propanol yielded pure 2-iodo-5-methoxy-N-alphadimethylbenzenepropanamine hydrochloride a white solid, mp 189°-190° C.

Aufarbeitung

  1. temperatureThe resulting mixture was cooled in an ice bath
  2. customThe solvent was evaporated in vacuo
  3. customthe residue partitioned between 1.5 l of water and 600 ml of ether
  4. customThe water layer was separated
  5. additiontreated with 50% sodium hydroxide solution until basic
  6. extractionThe resulting crude product was extracted into 500 ml of ether
  7. washwashed with brine
  8. extractionthe brine layer extracted with an additional 400 ml portion of ether
  9. dry with materialThe combined ether layers were dried over anhydrous potassium carbonate
  10. customevaporated in vacuo
  11. customto yield 31.09 g (78%) of crude oil
  12. customthe resulting hydrochloride salt separated by filtration

Quellen und Nachweise

ORD-Eintrag
ord-4b56e1a1eb2749f9921e145bdf7fa44d
Quelldatensatz
uspto-grants-1987_04
Patentnummer
US04661635

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