Triethylamine → HCID 86681323, compound

HRID 1430296Notes

Reaction equation

HRID 1430296 reaction equation
Cl.[NH2:2][C:3]1([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.C(N(CC)CC)C.Br[CH2:22][CH2:23][O:24][CH2:25][CH2:26]Br>CN(C)C=O.C(OCC)(=O)C>[O:24]1[CH2:25][CH2:26][N:2]([C:3]2([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]2)[CH2:22][CH2:23]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 21521Bis(2-bromoethyl) etherHCID 11241228Ethyl 1-aminocyclohexane-1-carboxylate hydrochloride

Product 1

HCID 86681323HCID 86681323, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ethyl 1-aminocyclohexancarboxylate hydrogen chloride (5.800 g), triethylamine (13.62 mL) and 1-bromo-2-(2-bromoethoxy)ethane (4.21 mL) were stirred together in N,N-dimethylformamide (50 mL) at 95° C. overnight. The reaction mixture was diluted with ethyl acetate (150 mL), washed with water (100 mL) and brine (100 mL), dried over magnesium sulfate, filtered, and concentrated. Silica gel chromatography eluting with a gradient of 5% to 25% ethyl acetate/hexanes provided the title compound.

Workup

  1. washwashed with water (100 mL) and brine (100 mL)
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. washSilica gel chromatography eluting with a gradient of 5% to 25% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-fb5412b24ac84b32bf114eacb4a68bbe
Source dataset
uspto-grants-2015_01
Patent number
US08940737B2

Reaction notes

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