Triethylamine → HCID 178453985, compound

HRID 574768Notes

Reaction equation

HRID 574768 reaction equation
[C:1]([O:5][C:6](=[O:15])[NH:7][CH:8]1[CH2:13][CH2:12][CH:11]([NH2:14])[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].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:14]([C@H:11]2[CH2:10][CH2:9][C@H:8]([NH:7][C:6](=[O:15])[O:5][C:1]([CH3:4])([CH3:2])[CH3:3])[CH2:13][CH2:12]2)[CH2:17][CH2:18]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21521Bis(2-bromoethyl) etherHCID 2756050Cis tert-Butyl 4-aminocyclohexylcarbamate

Product 1

HCID 178453985HCID 178453985, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of tert-butyl-4-aminocyclohexylcarbamate (20.32 g, 95 mmol), bis(2-bromoethyl)ether (14.30 ml, 114 mmol) and triethylamine (33.0 ml, 237 mmol) in N,N-dimethylformamide (200 ml) was stirred for 16 hours at 70° C. The reaction mixture was cooled down to room temperature, concentrated and the product was extracted with ethyl acetate. The organic layer was washed with sodium carbonate solution (15% aq.), dried and concentrated. The product was used in next step without purification.

Workup

  1. concentrationconcentrated
  2. extractionthe product was extracted with ethyl acetate
  3. washThe organic layer was washed with sodium carbonate solution (15% aq.)
  4. customdried
  5. concentrationconcentrated
  6. customThe product was used in next step without purification

Sources & evidence

ORD record
ord-cb1806a0fb3f40909ea762d33ee29f28
Source dataset
uspto-grants-2015_05
Patent number
US09034875B2

Reaction notes

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