Diisopropylethylamine → HCID 22591702, compound

HRID 22835Notes

Reaction equation

HRID 22835 reaction equation
[CH:1]([N:4](CC)C(C)C)(C)C.[CH2:10]([C:15]12[CH2:22][CH2:21][C:18]([C:23]([OH:25])=O)([CH2:19][CH2:20]1)[CH2:17][CH2:16]2)[CH2:11][CH2:12][CH2:13][CH3:14].Cl.CN>C(Cl)Cl>[CH3:1][NH:4][C:23]([C:18]12[CH2:21][CH2:22][C:15]([CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])([CH2:20][CH2:19]1)[CH2:16][CH2:17]2)=[O:25]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 42414664-Pentylbicyclo[2.2.2]octane-1-carboxylic acidHCID 6364545Methylamine hydrochloride

Product 1

HCID 22591702HCID 22591702, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N,N-Diisopropylethylamine (1.44 mL, 11.1 mmol) was added to a mixture of 4-pentylbicyclo[2.2.2]octane-1-carboxylic acid (3-A) (1.09 g, 4.45 mmol) and methylamine hydrochloride (1.5 g, 22.3 mmol) in methylene chloride (10 mL) was added and the mixture stirred at room temperature for 18 h. After diluting with methylene chloride, the mixture was washed with water, brine, dried (MgSO4) and concentrated in vacuo to give N-methyl-4-pentylbicyclo[2.2.2]octane-1-carboxamide (3-C). 1H NMR (500 MHz, CDCl3): δ 0.91 (t, 3H); 1.22 (m, 8M); 1.43 (m, 6H); 1.77 (m, 6H); 2.82 (d, 3H) ppm.

Workup

  1. additionwas added
  2. washthe mixture was washed with water, brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-40ea1257b65d4cb6805dab6fe406ea45
Source dataset
uspto-grants-2005_02
Patent number
US06849636B2

Reaction notes

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