Dimethylamine → HCID 57750395, compound

HRID 423051Notes

Reaction equation

HRID 423051 reaction equation
CS(O[CH2:6][CH2:7][CH:8]([NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1)(=O)=O.C1COCC1.[CH3:29][NH:30][CH3:31]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:15][C:12]1[CH:13]=[CH:14][C:9]([CH:8]([NH:16][C:17](=[O:18])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:7][CH2:6][N:30]([CH3:31])[CH3:29])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 57750403HCID 57750403, compound2×

Product 1

HCID 57750395HCID 57750395, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 67553Tetrabutylammonium IodideCatalyst

Conditions

Temperature
150 °C

Procedure

3-(tert-Butoxycarbonylamino)-3-(4-chlorophenyl)propyl methanesulfonate (Intermediate 31) (0.075 g, 0.21 mmol) and tetrabutylammonium iodide (0.015 g, 0.04 mmol) were dissolved in a solution of dimethylamine in THF (2M, 5.153 mL, 10.31 mmol) and sealed into a microwave tube. The reaction was heated to 150° C. for 30 minutes in the microwave reactor and cooled to ambient temperature. The reaction mixture was concentrated, diluted with DCM (25 mL) and washed with water (25 mL). The organic layer was filtered through a phase-separating filter paper and evaporated. The crude product was purified by flash silica chromatography, elution gradient 4 to 8% (10:1 MeOH/conc. NH3 (aq)) in DCM. Pure fractions were evaporated to dryness to afford tert-butyl 1-(4-chlorophenyl)-3-(dimethylamino)propylcarbamate (0.054 mg, 84%) as a colourless oil.

Workup

  1. customsealed into a microwave tube
  2. temperaturecooled to ambient temperature
  3. concentrationThe reaction mixture was concentrated
  4. additiondiluted with DCM (25 mL)
  5. washwashed with water (25 mL)
  6. filtrationThe organic layer was filtered through a phase-separating
  7. filtrationfilter paper
  8. customevaporated
  9. customThe crude product was purified by flash silica chromatography, elution gradient 4 to 8% (10:1 MeOH/conc. NH3 (aq)) in DCM
  10. customPure fractions were evaporated to dryness

Sources & evidence

ORD record
ord-cfbf9e62b1b54cc691ed3419e6f073f1
Source dataset
uspto-grants-2012_01
Patent number
US08101623B2

Reaction notes

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