Butanal → 4-[3-(4-Butylpiperazin-1-yl)-4-(3,3,5,5-tetramethylcyclohexyl)phenyl]morpholine

HRID 2218851Notes

Reaction equation

HRID 2218851 reaction equation
[N:1]1([C:7]2[CH:8]=[C:9]([N:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)[CH:10]=[CH:11][C:12]=2[CH:13]2[CH2:18][C:17]([CH3:20])([CH3:19])[CH2:16][C:15]([CH3:22])([CH3:21])[CH2:14]2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[CH:29](=O)[CH2:30][CH2:31][CH3:32].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>C(OCC)(=O)C.O1CCCC1>[CH2:29]([N:4]1[CH2:3][CH2:2][N:1]([C:7]2[CH:8]=[C:9]([N:23]3[CH2:24][CH2:25][O:26][CH2:27][CH2:28]3)[CH:10]=[CH:11][C:12]=2[CH:13]2[CH2:14][C:15]([CH3:21])([CH3:22])[CH2:16][C:17]([CH3:20])([CH3:19])[CH2:18]2)[CH2:6][CH2:5]1)[CH2:30][CH2:31][CH3:32]

Participants

7

Reactant 4

HCID 261ButanalHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 231426114-[3-Piperazin-1-yl-4-(3,3,5,5-tetramethylcyclohexyl)phenyl]morpholine

Product 1

HCID 231418294-[3-(4-Butylpiperazin-1-yl)-4-(3,3,5,5-tetramethylcyclohexyl)phenyl]morpholine

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 4-[3-piperazin-1-yl-4-(3,3,5,5-tetramethylcyclohexyl)phenyl]morpholine (14 mg, 0.0363 mmol) produced in Example (81e), butyraldehyde (0.0097 mL, 0.109 mmol) and tetrahydrofuran (0.5 mL) was added sodium triacetoxyborohydride (23 mg, 0.109 mmol), followed by stirring for 1 hour and 30 minutes at room temperature. Saturated aqueous solution of sodium hydrogencarbonate was added to the reaction mixture and extraction was performed with ethyl acetate. The solvent was distilled of by nitrogen stream to the separated organic layer. The resultant residue was purified by NH silica gel column chromatography (ethyl acetate/heptane) to give 4-[3-(4-butylpiperazine-1-yl)-4-(3,3,5,5-tetramethylcyclohexyl)phenyl]morpholine.

Workup

  1. distillationThe solvent was distilled of by nitrogen stream to the separated organic layer
  2. customThe resultant residue was purified by NH silica gel column chromatography (ethyl acetate/heptane)

Sources & evidence

ORD record
ord-bd9c36bb355a4217adc1c8e0bd4c6f5a
Source dataset
uspto-grants-2008_08
Patent number
US07410971B2

Reaction notes

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