Acetic Acid → (1-Benzylpiperidin-4-yl)-[2-(5-methoxy-2-nitrophenyl)-ethyl]-amine

HRID 469289

Reaktionsgleichung

[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N+:12]([O-:14])=[O:13])=[C:7]([CH2:9][CH2:10][NH2:11])[CH:8]=1.[CH2:15]([N:22]1[CH2:27][CH2:26][CH2:25][CH2:24][C:23]1=O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl>[CH2:15]([N:22]1[CH2:27][CH2:26][CH:25]([NH:11][CH2:10][CH2:9][C:7]2[CH:8]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]=2[N+:12]([O-:14])=[O:13])[CH2:24][CH2:23]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

Under a nitrogen atmosphere a mixture of 9.98 g (50.9 mmol) 2-(5-methoxy-2-nitrophenyl)-ethylamine, 9.80 mL (54.9 mmol) N-benzylpiperidone and 6.30 mL (114 mmol) acetic acid in 270 mL DCM was cooled to 0° C. in an ice bath. At this temperature 14.2 g (67.0 mmol) sodium triacetoxyborohydride were added batchwise within 20 min. The reaction mixture was stirred for a further 4 h at 0° C. and left to warm up to RT overnight. Then the mixture was combined with 400 mL of a 15% (w/v) aqueous potassium carbonate solution and stirred for 1 h at RT. The organic phase was separated off, dried and concentrated by rotary evaporation. 18.8 g of the desired product were obtained.

Aufarbeitung

waitleft
temperatureto warm up to RT overnight
stirringstirred for 1 h at RT
customThe organic phase was separated off
customdried
concentrationconcentrated by rotary evaporation

Quellen und Nachweise

ORD-Eintrag: ord-3e1c2f221c9e4506885fd66d5bd83c5b
Quelldatensatz: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08629137B2

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