Triethylamine → HCID 68137177, Verbindung

HRID 1578932

Reaktionsgleichung

Reaktionsgleichung von HRID 1578932
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[CH:12]=O.C(N(CC)CC)C.[ClH:21].[NH2:22][CH:23]([CH3:32])[CH:24]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[OH:25].[BH4-].[Na+]>CO.O>[ClH:21].[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[CH2:12][NH:22][CH:23]([CH3:32])[CH:24]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[OH:25]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 90652-Amino-1-phenylpropan-1-ol hydrochlorideHCID 769091-Bromonaphthalene-2-carbaldehydeHCID 4311764Sodium borohydride

Produkt 1

HCID 68137177HCID 68137177, VerbindungAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 38.4 g (0.164 mole) 1-bromo-2-naphthaldehyde, 16.4g (0.164 mole) triethylamine, and 30.6 g (0.164 mole) of 2-amino-1-phenyl-1-propanol hydrochloride in 500 ml CH3OH was stirred and refluxed for 60 minutes, then cooled to 10°-20° while 6.23 g (0.164 mole) of sodium borohydride was added over 5 minutes. The reaction mixture was stirred at ambient temperature (15°-21°) for 60 minutes and diluted with 500 ml H2O. The mixture was stirred for 15 minutes and extracted with 2 × 350 ml CHCl3. The combined extracts were dried (MgSO4) and concentrated to dryness in vacuo to give 59.6 g (99%) of the free base.

Aufarbeitung

  1. temperaturerefluxed for 60 minutes
  2. additionwas added over 5 minutes
  3. stirringThe reaction mixture was stirred at ambient temperature (15°-21°) for 60 minutes
  4. stirringThe mixture was stirred for 15 minutes
  5. extractionextracted with 2 × 350 ml CHCl3
  6. dry with materialThe combined extracts were dried (MgSO4)
  7. concentrationconcentrated to dryness in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f5b6f536c98b4b79a918a716e1739155
Quelldatensatz
uspto-grants-1976_02
Patentnummer
US03940400

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