Hydrochloric Acid → 4-[4-[8-(2,6-Dimethylmorpholin-4-yl)octyloxy]phenyl]benzoic acid hydrochloride

HRID 1872406Notes

Reaction equation

HRID 1872406 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:25]=[CH:24][C:20]([C:21]([OH:23])=[O:22])=[CH:19][CH:18]=2)=[CH:13][CH:12]=1.O.C(OCC)(=O)C.[ClH:33].[CH3:34][CH:35]1[O:40][CH:39]([CH3:41])[CH2:38][NH:37][CH2:36]1>>[ClH:33].[CH3:41][CH:39]1[O:40][CH:35]([CH3:34])[CH2:36][N:37]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:25]=[CH:24][C:20]([C:21]([OH:23])=[O:22])=[CH:19][CH:18]=3)=[CH:13][CH:12]=2)[CH2:38]1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 8857Ethyl AcetateHCID 1108622,6-DimethylmorpholineHCID 211822604-[4-(8-Bromooctyloxy)phenyl]benzoic acid

Product 1

HCID 700603274-[4-[8-(2,6-Dimethylmorpholin-4-yl)octyloxy]phenyl]benzoic acid hydrochloride

Procedure

A suspension of 4-[4-(8-bromooctyloxy)phenyl]benzoic acid (1 g) in 2,6-dimethylmorpholine (3.06 ml) was refluxed for 30 minutes. The reaction mixture was added to a mixture of water and ethyl acetate and adjusted to pH 2.0 with conc. HCl. The organic layer was taken and dried over magnesium sulfate. The magnesium sulfate was filtered off, and the filtrate was evaporated under reduced pressure to give 4-[4-[8-(2,6-dimethylmorpholin-4-yl)octyloxy]phenyl]benzoic acid hydrochloride (0.95 g).

Workup

  1. temperaturewas refluxed for 30 minutes
  2. dry with materialdried over magnesium sulfate
  3. filtrationThe magnesium sulfate was filtered off
  4. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-3a36a55a48764fb5a68f546f39383296
Source dataset
uspto-grants-2000_08
Patent number
US06107458

Reaction notes

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