1,1-Dichloroethane → HCID 54267912, compound

HRID 429844Notes

Reaction equation

HRID 429844 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([NH:11][C:12]2[CH:13]=[C:14]([CH2:18][C@H:19]([NH:21][CH2:22][CH2:23][CH3:24])[CH3:20])[CH:15]=[CH:16][CH:17]=2)=[O:10])=[CH:5][CH:4]=1.ClC(Cl)C.[N:29]1([C:35]([N:37]2[CH2:42][CH2:41][CH:40]([CH:43]=O)[CH2:39][CH2:38]2)=[O:36])[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(OCC)C.[OH-].[Na+]>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]([NH:11][C:12]2[CH:13]=[C:14]([CH2:18][C@H:19]([N:21]([CH2:43][CH:40]3[CH2:41][CH2:42][N:37]([C:35]([N:29]4[CH2:34][CH2:33][O:32][CH2:31][CH2:30]4)=[O:36])[CH2:38][CH2:39]3)[CH2:22][CH2:23][CH3:24])[CH3:20])[CH:15]=[CH:16][CH:17]=2)=[O:10])=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 63651,1-DichloroethaneHCID 5049666Sodium triacetoxyborohydrideHCID 18352829HCID 18352829, compoundHCID 54568336HCID 54568336, compound

Product 1

HCID 54267912HCID 54267912, compoundYield 79.8%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 14798Sodium HydroxideSolvent

Procedure

(R)-N-{2-[3-(4-Methoxyphenylcarbonylamino)phenyl]-1-methylethyl}-propylamine (0.32 g), dichloroethane (20 ml) and 1-(morpholine-4-carbonyl)piperidine-4-carboxaldehyde (0.32 g) and were stirred under nitrogen for 30 minutes. Sodium triacetoxyborohydride (0.5 g) was added, and the mixture stirred at room temperature for about 72 hours. The mixture was diluted with diethyl ether (50 ml) and 10% sodium hydroxide solution (20 ml). The organic layer was dried with sodium sulfate, filtered, and the solvent evaporated in vacuo. The residue was chromatographed, eluting with methanol/dichloromethane to give (R)-N-{2-[3-(4-methoxyphenylcarbonylamino)phenyl]-1-methylethyl}-N-propyl-[1-(morpholine-4-carbonyl)piperidine-4-ylmethyl]amine, (0.42 g), [α]D25−42° (c 1.0 CH3OH); M+H 537.

Workup

  1. dry with materialThe organic layer was dried with sodium sulfate
  2. filtrationfiltered
  3. customthe solvent evaporated in vacuo
  4. customThe residue was chromatographed
  5. washeluting with methanol/dichloromethane

Sources & evidence

ORD record
ord-c89f29f6bbf94764be5e797cccc96132
Source dataset
uspto-grants-2001_11
Patent number
US06319920B1

Reaction notes

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