Dipropargylamine → 2,4-Bis-benzyloxy-5-isopropenyl-N,N-di-prop-2-ynyl-benzamide

HRID 241829Notes

Reaction equation

HRID 241829 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[C:16]([O:18][CH2:19]C2C=CC=CC=2)[C:15]([C:26]([CH3:28])=[CH2:27])=[CH:14][C:10]=1[C:11]([OH:13])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.C(N=C=NCCCN(C)C)C.ON1[C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][C:45]=2N=N1.[CH2:51]([NH:54][CH2:55][C:56]#[CH:57])[C:52]#[CH:53]>ClCCl>[CH2:1]([O:8][C:9]1[CH:17]=[C:16]([O:18][CH2:19][C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[C:15]([C:26]([CH3:28])=[CH2:27])=[CH:14][C:10]=1[C:11]([N:54]([CH2:55][C:56]#[CH:57])[CH2:51][C:52]#[CH:53])=[O:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 23350DipropargylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 498640162,4-Bis(benzyloxy)-5-isopropenylbenzoic acid

Product 1

HCID 581575202,4-Bis-benzyloxy-5-isopropenyl-N,N-di-prop-2-ynyl-benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of 2,4-bis-benzyloxy-5-isopropenyl-benzoic acid (Example 1 Step 6) (1 equivalent) in dichloromethane (10 ml) was treated successively with N-ethyl-N′-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.2 equivalents), 1-hydroxybenzotriazole (1.2 equivalents) and dipropargylamine (1.5 equivalents) and the mixture was stirred at room temperature overnight. The mixture was washed successively with 2M hydrochloric acid and 2M sodium hydroxide, the organic layer was separated and the solvent removed in vacuo to afford the product which was either obtained pure or was purified by column chromatography on silica (eluting with mixtures of ethyl acetate in petroleum ether or methanol in ethyl acetate as appropriate). MS: [M+H]+ 450

Workup

  1. washThe mixture was washed successively with 2M hydrochloric acid and 2M sodium hydroxide
  2. customthe organic layer was separated
  3. customthe solvent removed in vacuo
  4. customto afford the product which
  5. customwas purified by column chromatography on silica (eluting with mixtures of ethyl acetate in petroleum ether or methanol in ethyl acetate as appropriate)

Sources & evidence

ORD record
ord-67924166b19a4afabc46ba53151dc276
Source dataset
uspto-grants-2014_02
Patent number
US08653084B2

Reaction notes

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