Tempo → 4-[2-[1-(Formylmethyl)cyclohexyl]ethyl]morpholine

HRID 1820297Notes

Reaction equation

HRID 1820297 reaction equation
CC1(C)N([O])C(C)(C)CCC1.[OH:12][CH2:13][CH2:14][C:15]1([CH2:21][CH2:22][N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1>C(Cl)Cl>[CH:13]([CH2:14][C:15]1([CH2:21][CH2:22][N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]1)=[O:12]

Participants

5

Reactant 3

HCID 2724126TempoHCID 12217721Iodo benzene diacetateHCID 231098894-[2-[1-(2-Hydroxyethyl)cyclohexyl]ethyl]morpholine

Product 1

HCID 231099074-[2-[1-(Formylmethyl)cyclohexyl]ethyl]morpholineYield 143.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

After adding 2,2,6,6-tetramethylpiperidine 1-oxyl free radical (32 mg, 0.20 mmol) to a solution of 4-[2-[1-(2-hydroxyethyl)cyclohexyl]ethyl]morpholine (439 mg, 1.82 mmol) and iodobenzene diacetate (644 mg, 2.00 mmol) in methylene chloride (10 mL), the mixture was stirred at room temperature for 14 hours. The reaction mixture was washed with saturated aqueous sodium hydrogencarbonate and saturated brine in that order and dried (anhydrous sodium sulfate), and then the solvent was distilled off under reduced pressure to obtain the title compound as a brown oil (625 mg). This was used without purification for the following step.

Workup

  1. washThe reaction mixture was washed with saturated aqueous sodium hydrogencarbonate and saturated brine in that order
  2. dry with materialdried (anhydrous sodium sulfate)
  3. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-41b51f89f7674113af74738cf6669414
Source dataset
uspto-grants-2009_10
Patent number
US07601843B2

Reaction notes

Loading…