Triethylamine → HCID 27550088, compound

HRID 2054558Notes

Reaction equation

HRID 2054558 reaction equation
[C:1](Cl)(=[O:6])[CH2:2][CH2:3][CH2:4][CH3:5].[C:8]12([C:18]([NH:20][NH2:21])=[O:19])[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2.C(N(CC)CC)C.C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:1]([NH:21][NH:20][C:18]([C:8]12[CH2:17][CH:12]3[CH2:11][CH:10]([CH2:16][CH:14]([CH2:13]3)[CH2:15]1)[CH2:9]2)=[O:19])(=[O:6])[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 61186Valeryl chlorideHCID 337203adamantane-1-carbohydrazideHCID 516892Sodium Bicarbonate

Product 1

HCID 27550088HCID 27550088, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Valeryl chloride (E) (0.981 mL, 8.1 mmol) was added dropwise to a solution of adamantane-1-carbohydrazide (F) (1.5 g, 7.72 mmol) and triethylamine (1.18 mL, 8.49 mmol) in methylene chloride (30 mL) at room temperature, and the mixture stirred at room temperature for 3.5 h. A solution of 10% NaHCO3 (15 mL) was added and the mixture stirred rapidly for 1.5 h. The mixture was extracted with methylene chloride (3×) and the combined extracts washed with water, dried (MgSO4) and concentrated in vacuo to give N′-pentanoyladamantane-1-carbohydrazide (G). 1H NMR (CDCl3): δ 0.94 (t, 3H); 1.38 (m, 2H); 1.75 (m, 8H); 1.93 (d, 6H); 2.08 (s, 3H); 2.29 (t, 2H); 8.47 (d, 1H); 8.7 (d, 1H).

Workup

  1. stirringthe mixture stirred rapidly for 1.5 h
  2. extractionThe mixture was extracted with methylene chloride (3×)
  3. washthe combined extracts washed with water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b2402957091b4dc990342930985d5150
Source dataset
uspto-grants-2008_02
Patent number
US07329683B2

Reaction notes

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