N,N-Dimethyl-N-decylamine → HCID 86612068, compound

HRID 1453413

Reaction equation

HRID 1453413 reaction equation
[CH3:1][N:2]([CH3:13])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[CH:14]([C:16]1[CH:23]=[CH:22][C:19]([CH2:20][Cl:21])=[CH:18][CH:17]=1)=[CH2:15]>CCOCC>[Cl-:21].[CH:14]([C:16]1[CH:23]=[CH:22][C:19]([CH2:20][N+:2]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])([CH3:1])[CH3:13])=[CH:18][CH:17]=1)=[CH2:15]

Participants

4

Reactant 2

HCID 70711N,N-Dimethyl-N-decylamineHCID 74126p-Vinylbenzyl chloride

Product 1

HCID 86612068HCID 86612068, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Dimethyl decyl amine (9.30 g, 50 mmol) and 4-vinylbenzylchloride (7.63 g, 50 mmol) were added to ether (20 mL) and were allowed to stir for 12 hours. A yellow solid precipitated and was subsequently collected by filtration resulting in 3 g (17% yield). The ether was removed and the remaining solution was allowed to react neat for 24 hours giving a near quantitative yield after washing with ether. Subsequent reactions were performed neat. 1H-NMR (90 MHz, CDCl3, δ): 7.68-7.38 (dd, 4H); 6.87-6.56 (dd, 1H); 5.89-5.70 (d, 1H); 5.41-5.29 (d, 1H); 5.09 (s, 2H); 3.51 (bs, 2H); 3.31 (s, 6H); 1.81 (bs, 2H) 1.25 (bs, 14H); 0.92-0.81 (t, 3H).

Workup

  1. customA yellow solid precipitated
  2. filtrationwas subsequently collected by filtration
  3. customresulting in 3 g (17% yield)
  4. customThe ether was removed
  5. customto react neat for 24 hours
  6. customgiving a near quantitative yield
  7. washafter washing with ether

Sources & evidence

ORD record
ord-776ffa8b5eef4b8dacc07dcaf477d530
Source dataset
uspto-grants-2009_01
Patent number
US07476316B2

Linked notes

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