Dimethylformamide → Tert-butyl N-{2-[(2-phenylethyl)amino]ethyl}carbamate

HRID 609645Notes

Reaction equation

HRID 609645 reaction equation
Cl.[C:2]1([CH2:8][CH2:9][NH2:10])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.BrC([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])CN.[C:22]([O-])([O-])=O.[K+].[K+].C[N:29]([CH:31]=O)C>>[C:18]([O:17][C:15](=[O:16])[NH:29][CH2:31][CH2:22][NH:10][CH2:9][CH2:8][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)([CH3:19])([CH3:20])[CH3:21]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 90752-Phenylethylamine hydrochlorideHCID 11430Potassium CarbonateHCID 866284082-bromo-N-tert-butyloxycarbonylethylamine

Product 1

HCID 10563596Tert-butyl N-{2-[(2-phenylethyl)amino]ethyl}carbamateYield 30%

Conditions

Temperature
60 °C

Procedure

A solution of phenylethylamine hydrochloride (2.88 g, 0.018 mol) and 2-bromo-N-tert-butyloxycarbonylethylamine (4.1 g, 0.018 mmol) in DMF (50 mL), containing K2CO3 (5.0 g, 0.036 mol), was heated at 60° C. for 4 h. The solution was filtered, evaporated and the residue partitioned between CH2Cl2 (2×100 mL) and water (100 mL). The combined organic layers were dried (Na2SO4) and evaporated. The residue was chromatographed on silica gel, eluting with CH2Cl2 :MeOH (90:10), to afford the title compound (1.44 g, 30%) as a colourless oil. 1H NMR (250 MHz, CDCl3) δ 1.44 (9H, s), 2.74 (2H, t, J=6.0Hz), 2.79 (2H, m), 2.88 (2H, m), 3.19 (2H, m), 4.87 (1H, br s), 7.19-7.22 (3H, m), 7.26-7.31 (2H, m). MS (ES+) (265, M+1).

Workup

  1. filtrationThe solution was filtered
  2. customevaporated
  3. customthe residue partitioned between CH2Cl2 (2×100 mL) and water (100 mL)
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. customevaporated
  6. customThe residue was chromatographed on silica gel
  7. washeluting with CH2Cl2 :MeOH (90:10)

Sources & evidence

ORD record
ord-f7ea5cef18154907ae67c1cadfe6df8c
Source dataset
uspto-grants-1999_12
Patent number
US05998415

Reaction notes

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