Dimethylamine → Tert-butyl 4-((dimethylamino)methyl)phenethylcarbamate

HRID 1021414Notes

Reaction equation

HRID 1021414 reaction equation
CS(O[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[CH:9][CH:8]=1)(=O)=O.[CH:23]([N:26](CC)[CH:27](C)C)(C)C.CNC>O1CCCC1>[CH3:23][N:26]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][NH:15][C:16](=[O:17])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:9][CH:8]=1)[CH3:27]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 81531DiisopropylethylamineHCID 86653235HCID 86653235, compound

Product 1

HCID 67080402Tert-butyl 4-((dimethylamino)methyl)phenethylcarbamateYield 54%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred suspension of 4-(2-(tert-butoxycarbonylamino)ethyl)benzyl methanesulfonate (0.33 g, 1.0 mmol) and N,N-diisopropylethylamine (0.19 mL, 1.1 mmol) in tetrahydrofuran (50 mL) was added a 2M solution of dimethylamine in tetrahydrofuran (5.0 mL, 10 mmol). The resulting mixture was stirred in an oil bath set to 60° C. for 6 hours. The solution was cooled to ambient temperature and concentrated. The residue was partitioned between ethyl acetate (20 mL) and water (10 mL). The organic layer was dried over sodium sulfate and concentrated. The residue was purified by chromatography on silica gel, eluting with 99/1 to 98/2 chloroform/(90/10 methanol/concentrated ammonium hydroxide), to afford tert-butyl 4-((dimethylamino)methyl)phenethylcarbamate as a colorless oil (0.15 g, 54% yield).

Workup

  1. concentrationconcentrated
  2. customThe residue was partitioned between ethyl acetate (20 mL) and water (10 mL)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography on silica gel
  6. washeluting with 99/1 to 98/2 chloroform/(90/10 methanol/concentrated ammonium hydroxide)

Sources & evidence

ORD record
ord-15babc6428934a1889457fa2af0b9810
Source dataset
uspto-grants-2014_05
Patent number
US08716498B2

Reaction notes

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