2-Bromoethyldimethylamine → HCID 67036842, compound

HRID 216072Notes

Reaction equation

HRID 216072 reaction equation
[N:1]1([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:6][CH2:5][CH:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:3][CH2:2]1.[Li+].CC([N-]C(C)C)C.Br[CH2:28][CH2:29][N:30]([CH3:32])[CH3:31]>C1COCC1>[CH3:31][N:30]([CH3:32])[CH2:29][CH2:28][C:4]1([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:3][CH2:2][N:1]([C:12]([O:14][C:15]([CH3:17])([CH3:16])[CH3:18])=[O:13])[CH2:6][CH2:5]1

Participants

5

Reactant 3

HCID 178642-BromoethyldimethylamineHCID 2724682Lithium diisopropylamideHCID 27588121-Tert-butyl 4-ethyl piperidine-1,4-dicarboxylate

Product 1

HCID 67036842HCID 67036842, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1-tert-butyl 4-ethyl piperidine-1,4-dicarboxylate (514 mg, 2 mmol) in THF (10 mL) at −78° C. was added dropwise LDA (1.5 M in cyclohexane, 2 mL, 3 mmol). After stirring for 30 minutes, 2-bromo-N,N-dimethylethanamine (370 mg, 2.4 mmol) in THF (3 mL) was added. The reaction was stirred for 30 min at −78° C., then allowed to warm to room temperature, stirred for 2 hours, then quenched with sat. aq. NaHCO3, diluted with EtOAc, washed with sat. aq. NaHCO3 and brine (with back extraction), dried over MgSO4, and concentrated under vacuum. The residue was purified by flash chromatography (40 g SiO2, 0-15% MeOH:CH2Cl2) to give the title compound (328 mg, 1.0 mmol, 50%) as a yellow oil. MS (ES+) [M+H]+=329.

Workup

  1. stirringThe reaction was stirred for 30 min at −78° C.
  2. stirringstirred for 2 hours
  3. customquenched with sat. aq. NaHCO3
  4. additiondiluted with EtOAc
  5. washwashed with sat. aq. NaHCO3 and brine (with back extraction)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under vacuum
  8. customThe residue was purified by flash chromatography (40 g SiO2, 0-15% MeOH:CH2Cl2)

Sources & evidence

ORD record
ord-a6aed3f2900b471d8fa8076e5baf4f9d
Source dataset
uspto-grants-2012_06
Patent number
US08193202B2

Reaction notes

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