Acetic Acid → Ammonia methanol dichloromethane

HRID 33698Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 33698
Cl.[N:2]1([CH2:7][CH2:8][CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)=[CH:13][CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3]1.[CH:23](=O)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl:49][CH:50]([Cl:52])C>>[NH3:2].[CH3:9][OH:10].[Cl:49][CH2:50][Cl:52].[CH2:23]([N:20]1[CH2:19][CH2:18][N:17]([C:14]2[CH:13]=[CH:12][C:11]([O:10][CH2:9][CH2:8][CH2:7][N:2]3[CH2:6][CH2:5][CH2:4][CH2:3]3)=[CH:16][CH:15]=2)[CH2:22][CH2:21]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Komponenten

7

Edukt 5

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 63651,1-DichloroethaneHCID 5049666Sodium triacetoxyborohydrideHCID 99018441-[4-(3-Pyrrolidin-1-yl-propoxy)-phenyl]-piperazine hydrochloride

Produkt 2

HCID 99699911-Benzyl-4-[4-(3-pyrrolidin-1-yl-propoxy)-phenyl]-piperazineHCID 21584172Ammonia methanol dichloromethaneAusbeute 5 %

Versuchsvorschrift

A solution of the product of Example 23 (148 mg), benzaldehyde (520 mg), and acetic acid (25 mg) in dichloroethane (3 mL) was treated with sodium triacetoxyborohydride (121 mg). After 14 h, the reaction was quenched with saturated aqueous sodium bicarbonate, and the aqueous phase was extracted with dichloromethane (120 mL). The organic phase was dried (magnesium sulfate) and evaporated in vacuo. Silica gel chromatography of the residue (5% 2M ammonia-methanol/dichloromethane) gave the title compound as a light yellow solid (8 mg). 1H NMR (400 MHz, CDCl3): 7.36-7.24 (m, 5H), 6.94-6.81 (m, 4H), 3.96 (t, J=6.4 Hz, 2H), 3.56 (s, 2H), 3.08 (t, J=4.9 Hz, 4H), 2.64-2.60 (m, 4H), 2.04-1.94 (m, 2H), 1.80-1.75 (m, 4H).

Aufarbeitung

  1. customthe reaction was quenched with saturated aqueous sodium bicarbonate
  2. extractionthe aqueous phase was extracted with dichloromethane (120 mL)
  3. dry with materialThe organic phase was dried (magnesium sulfate)
  4. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-accdf9f94e824b48ab1a2eac8bb2b6b7
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07429586B2

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