Diisopropylethylamine → HCID 21993968, compound

HRID 1978335Notes

Reaction equation

HRID 1978335 reaction equation
Cl.[NH2:2][CH:3]1[CH2:8][CH2:7][CH:6]([C:9]([O:11][CH3:12])=[O:10])[CH2:5][CH2:4]1.Br[CH2:14][CH2:15][CH:16]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:17][CH2:18]Br.C(N(CC)C(C)C)(C)C.C(=O)([O-])O.[Na+]>C(#N)C>[C:20]1([CH:16]2[CH2:17][CH2:18][N:2]([CH:3]3[CH2:4][CH2:5][CH:6]([C:9]([O:11][CH3:12])=[O:10])[CH2:7][CH2:8]3)[CH2:14][CH2:15]2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 563261HCID 563261, compoundHCID 18521575Methyl 4-aminocyclohexane-1-carboxylate--hydrogen chloride (1/1)

Product 1

HCID 21993968HCID 21993968, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 3.896 g (20.117 mM) of methyl 4-aminocyclohexanecarboxylate hydrochloride, 6.77 g (22.1 mM) of 1,5-dibromo-3-phenylpentane, and 14.0 ml (80.5 mM) of N,N-diisopropylethylamine in 100 ml of acetonitrile was refluxed for one day. This reaction mixture was poured in aqueous solution of sodium hydrogen carbonate and extracted with 3 portions of ethyl acetate. The organic layers were pooled and dried over MgSO4 and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1 to 1/1) to provide the title compound.

Workup

  1. extractionextracted with 3 portions of ethyl acetate
  2. dry with materialdried over MgSO4
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1 to 1/1)

Sources & evidence

ORD record
ord-3ffaec638abc4d77ad3b9ce8ea25ccf4
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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