Sodium Hydroxide → 1,3-Cyclohexanediol, 6-[(dimethylamino)methyl]-1-(3-methoxyphenyl)-

HRID 2358478Notes

Reaction equation

HRID 2358478 reaction equation
[CH3:1][N:2]([CH2:4][CH:5]1[CH2:10][CH2:9][C:8](=[O:11])[CH2:7][C:6]1([OH:20])[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=1)[CH3:3].[BH4-].[Na+].[Cl-].[NH4+].[OH-].[Na+]>O1CCCC1.C(O)C>[CH3:3][N:2]([CH2:4][CH:5]1[C:6]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=2)([OH:20])[CH2:7][CH:8]([OH:11])[CH2:9][CH2:10]1)[CH3:1]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 9900270HCID 9900270, compound

Product 1

HCID 113004481,3-Cyclohexanediol, 6-[(dimethylamino)methyl]-1-(3-methoxyphenyl)-Yield 99.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 10 g (0.036 mol) of the crude product (IV) in 36.5 ml tetrahydrofuran was added dropwise at +2° C. with stirring to a solution of 1.36 g (0.036 mol, 1 equiv.) sodium borohydride in 15 ml ethanol and 36.5 ml tetrahydrofuran. Once the crude product solution had been completely added the mixture was then stirred for 60 to 90 minutes at +15° C. 25 ml aqueous ammonium chloride solution (10% w/w) were then added and alkalized with 5 ml sodium hydroxide solution (32%) to pH 12. After being extracted twice with 50 ml ethyl acetate, the combined phases were dried over magnesium sulfate and evaporated in vacuo. 10 g crude mixture was obtained in this case.

Workup

  1. extractionAfter being extracted twice with 50 ml ethyl acetate
  2. dry with materialthe combined phases were dried over magnesium sulfate
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-44b1f73e0f9847659ce695baca92185d
Source dataset
uspto-grants-2010_07
Patent number
US07763754B2

Reaction notes

Loading…