Sodium Bicarbonate → HCID 19938163, compound

HRID 36443Notes

Reaction equation

HRID 36443 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.[H][H].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 178418361HCID 178418361, compound

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 bromideacetic 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-729a5eb0812947ee9f16cdb7b886b986
Source dataset
uspto-grants-1995_05
Patent number
US05413997

Reaction notes

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