Triethylamine → HCID 178453985, compound

HRID 1043150Notes

Reaction equation

HRID 1043150 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:4][CH2:3]1.Br[CH2:17][CH2:18][O:19][CH2:20][CH2:21]Br.C(N(CC)CC)C>CN(C)C=O>[O:19]1[CH2:20][CH2:21][N:1]([C@H:2]2[CH2:7][CH2:6][C@H:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])[CH2:4][CH2:3]2)[CH2:17][CH2:18]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21521Bis(2-bromoethyl) etherHCID 178419079HCID 178419079, compound

Product 1

HCID 178453985HCID 178453985, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of tert-butyl trans-4-aminocyclohexylcarbamate (20.32 g), 1-bromo-2-(2-bromoethoxy)ethane (14.30 mL) and triethylamine (33.0 mL) in N,N-dimethylformamide (200 mL) was stirred for 16 hours at 70° C. The reaction mixture was cooled to room temperature and concentrated and the product was extracted with ethyl acetate. The organic layer was washed with sodium carbonate solution (15% aq.), dried (Na2SO4) and concentrated to give the title compound.

Workup

  1. concentrationconcentrated
  2. extractionthe product was extracted with ethyl acetate
  3. washThe organic layer was washed with sodium carbonate solution (15% aq.)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-db761f6ffc384e80ae489c073786df0a
Source dataset
uspto-grants-2013_10
Patent number
US08557983B2

Reaction notes

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