N,N-Diethylethylenediamine → HCID 12112112, compound

HRID 480194

Reaction equation

HRID 480194 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:11][C:12]([N:14]2[CH2:19][C@H:18]([CH3:20])[N:17]([CH2:21][C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)[CH2:16][C@H:15]2[CH3:29])=[O:13])=[C:6]([CH:9]=1)[CH:7]=O.C(O)(=O)C.ClC(Cl)C.[CH2:38]([N:40]([CH2:43][CH2:44][NH2:45])[CH2:41][CH3:42])[CH3:39].C([BH3-])#N.[Na+].C(=O)(O)[O-].[Na+]>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:11][C:12]([N:14]2[CH2:19][C@H:18]([CH3:20])[N:17]([CH2:21][C:22]3[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=3)[CH2:16][C@H:15]2[CH3:29])=[O:13])=[C:6]([CH2:7][NH:45][CH2:44][CH2:43][N:40]([CH2:41][CH3:42])[CH2:38][CH3:39])[CH:9]=1

Participants

7

Reactant 5

HCID 60993N,N-DiethylethylenediamineHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 18768099HCID 18768099, compoundHCID 53673807(2R,5S)-5-Chloro-2-{2-[4-(4-fluoro-benzyl)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-benzaldehyde

Product 1

HCID 12112112HCID 12112112, compoundYield 30.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of (2R,5S)-5-chloro-2-{2-[4-(4-fluoro-benzyl)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-benzaldehyde (0.100 g, 0.25 mmol) in 10:1 dichloroethane acetic acid (2.2 mL) was added (diethylamino)ethylamine (0.088 mL, 0.625 mmol) and the resulting solution was stirred for 1 hour at ambient temperature. To this was added sodium cyanoborohydride (0.0094 g, 0.15 mmol) and the reaction was stirred overnight at ambient temperature. Upon completion water was added and the mixture was basified with solid sodium bicarbonate (pH>10). The product was extracted with dichloromethane (2×) and diethyl ether (2×). The combined organics were dried over magnesium sulfate, filtered and concentrated in vacuo. Chromatography on silica gel gave the title compound (0.039 g, x 30% yield)

Workup

  1. stirringthe reaction was stirred overnight at ambient temperature
  2. extractionThe product was extracted with dichloromethane (2×) and diethyl ether (2×)
  3. dry with materialThe combined organics were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dba56af168444ddabdea68328ee57ade
Source dataset
uspto-grants-2003_11
Patent number
US06649611B2

Linked notes

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