1,2-Dichloroethane → HCID 117667273, compound

HRID 1526201Notes

Reaction equation

HRID 1526201 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:20][CH2:19][C:13]3([NH:18][CH2:17][CH2:16][CH2:15][CH2:14]3)[CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].C=O.Cl[CH2:24]CCl.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>O>[CH3:24][N:18]1[C:13]2([CH2:19][CH2:20][N:10]([C:7]3[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=3)[CH2:11][CH2:12]2)[CH2:14][CH2:15][CH2:16][CH2:17]1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 117667121HCID 117667121, compound

Product 1

HCID 117667273HCID 117667273, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 9-(4-nitrophenyl)-1,9-diazaspiro[5.5]undecane (680 mg), 37% aqueous formaldehyde solution (1 mL), and 1,2-dichloroethane (10 mL) was added sodium triacetoxyborohydride (1.57 g), followed by stirring at room temperature overnight. To the reaction mixture were added water and a saturated aqueous sodium hydrogen carbonate solution, followed by extraction with chloroform twice. The extract was dried over anhydrous sodium sulfate and then the solvent was evaporated under reduced pressure to obtain 1-methyl-9-(4-nitrophenyl)-1,9-diazaspiro[5.5]undecane (0.68 g) as a yellow solid.

Workup

  1. extractiona saturated aqueous sodium hydrogen carbonate solution, followed by extraction with chloroform twice
  2. dry with materialThe extract was dried over anhydrous sodium sulfate
  3. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-bd527d6ce43c41a19ded1d46a774cb8b
Source dataset
uspto-grants-2015_07
Patent number
US09085540B2

Reaction notes

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