Dimethylamine, hydrochloride → HCID 23457826, compound

HRID 1680289Notes

Reaction equation

HRID 1680289 reaction equation
[CH2:1]([NH:17][C:18]1[CH:31]=[CH:30][C:21]([C:22]([O:24][CH:25]([C:27](Cl)=[O:28])[CH3:26])=[O:23])=[CH:20][CH:19]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].Cl.[CH3:33][NH:34][CH3:35]>N1C=CC=CC=1>[CH2:1]([NH:17][C:18]1[CH:31]=[CH:30][C:21]([C:22]([O:24][CH:25]([C:27](=[O:28])[N:34]([CH3:35])[CH3:33])[CH3:26])=[O:23])=[CH:20][CH:19]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

4

Reactant 2

HCID 10473Dimethylamine, hydrochlorideHCID 23457763HCID 23457763, compound

Product 1

HCID 23457826HCID 23457826, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 3 g. (6.32 m moles) 1-(chlorocarbonyl)ethyl 4-(hexadecylamino)benzoate in 25 ml. pyridine is added 0.6 g. (7.5 m moles) dimethylamine hydrochloride. The solution is stirred at 50° C. for 15 hours, then evaporated to dryness. The residue is partitioned between 50 ml. water and 50 ml. methylene chloride. The layers are separated, and the aqueous solution is washed once more with 50 ml. methylene chloride. The combined organic solutions are dried, condensed, and the residue is crystallized from acetonitrile to yield the title compound as colorless crystals.

Workup

  1. customevaporated to dryness
  2. customThe residue is partitioned between 50 ml
  3. customThe layers are separated
  4. washthe aqueous solution is washed once more with 50 ml
  5. customThe combined organic solutions are dried
  6. customcondensed
  7. customthe residue is crystallized from acetonitrile

Sources & evidence

ORD record
ord-cc7f54c565b64e558867c66e37e8b860
Source dataset
uspto-grants-1981_06
Patent number
US04272546

Reaction notes

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