Sodium Bicarbonate → HCID 19938163, compound

HRID 1196160Notes

Reaction equation

HRID 1196160 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([C:32]2[CH:37]=[CH:36][C:35]([O:38]CC3C=CC=CC=3)=[CH:34][CH:33]=2)[C:16]2[CH:31]=[CH:30][CH:29]=[CH:28][C:17]=2[CH2:18][NH:19][CH:20]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)=[CH:11][CH:10]=1)C1C=CC=CC=1.Br.C(O)(=O)C.C(=O)([O-])O.[Na+]>>[CH:20]1([NH:19][CH2:18][C:17]2[CH:28]=[CH:29][CH:30]=[CH:31][C:16]=2[CH:15]([C:12]2[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][CH:13]=2)[C:32]2[CH:33]=[CH:34][C:35]([OH:38])=[CH:36][CH:37]=2)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]1

Participants

4

Reactant 3

HCID 516892Sodium Bicarbonate2×HCID 199381232-[Bis(4-benzyloxyphenyl)methyl]-N-(cyclooctyl)benzylamineHCID 21893785Acetic Acid Mixture with Hydrobromic Acid

Product 1

HCID 19938163HCID 19938163, compoundYield 54.5%

Procedure

Two grams of 2-[bis(4-benzyloxyphenyl)methyl]-N-(cyclooctyl)benzylamine obtained by Example 82 was dissolved in 120 ml of a mixture of ice-cooled hydrogen bromide-acetic acid solution. The solution was stirred for 2 hours, and the mixture was added to a mixture of ice and a saturated aqueous sodium hydrogencarbonate, stirred and then neutralized with sodium hydrogencarbonate. Thereafter, it was extracted with ethyl acetate, washed with water and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was subjected to recrystallization to afford 0.76 g of the desired compound (Compound 85).

Workup

  1. additionthe mixture was added to a mixture of ice
  2. extractionThereafter, it was extracted with ethyl acetate
  3. washwashed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was subjected to recrystallization

Sources & evidence

ORD record
ord-db1a29f8664f44d9b4e47e773eadd09e
Source dataset
uspto-grants-1992_05
Patent number
US05112867

Reaction notes

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