Triethylamine → N-(adamantan-2-yl)prop-2-enamide

HRID 5497

Reaction equation

HRID 5497 reaction equation
[C:1](Cl)(=[O:4])[CH:2]=[CH2:3].Cl.[CH:7]12[CH2:16][CH:11]3[CH2:12][CH:13]([CH2:15][CH:9]([CH2:10]3)[CH:8]1[NH2:17])[CH2:14]2.C(N(CC)CC)C>C(OCC)C.C(Cl)Cl>[CH:7]12[CH2:16][CH:11]3[CH2:12][CH:13]([CH2:15][CH:9]([CH2:10]3)[CH:8]1[NH:17][C:1](=[O:4])[CH:2]=[CH2:3])[CH2:14]2

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 253312-Aminoadamantane hydrochloride

Product 1

HCID 14986569N-(adamantan-2-yl)prop-2-enamide

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A solution of acryloyl chloride (4.52 g, 0.05 mole) in ethyl ether (20 ml) was added dropwise to a stirring mixture of 2-adamantylamine hydrochloride (9.35 g, 0.05 mole) and triethylamine (30.65 ml) in methylene chloride (200 ml) and ethyl ether (200 ml) over a 30 minute period. The solution was stirred for 12 hours, the solid filtered and washed with ethyl ether and the filtrate stripped to an oily material which was taken up in ethyl acetate and hexane and allowed to stand overnight. The solid was filtered, the filtrate concentrated and chilled and the product as an orange solid filtered and dried. The structure was confirmed by NMR.

Workup

  1. filtrationthe solid filtered
  2. washwashed with ethyl ether
  3. waitto stand overnight
  4. filtrationThe solid was filtered
  5. concentrationthe filtrate concentrated
  6. temperaturechilled
  7. filtrationthe product as an orange solid filtered
  8. customdried

Sources & evidence

ORD record
ord-2ab50f00f4ee40f3872001d53d2b0523
Source dataset
uspto-grants-1993_09
Patent number
US05244899

Linked notes

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