Sodium Hydroxide → HCID 24956860, compound

HRID 1095571Notes

Reaction equation

HRID 1095571 reaction equation
[CH3:1][N:2]([CH3:27])[C:3]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:8][CH2:7][C:6]([C:9]2[NH:10][C:11]3[C:16]([C:17]=2[CH2:18][CH2:19][CH3:20])=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:5][CH2:4]1.[Sn].[OH-].[Na+]>Br.C(Cl)Cl>[CH3:27][N:2]([CH3:1])[C:3]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:4][CH2:5][CH:6]([C:9]2[NH:10][C:11]3[C:16]([C:17]=2[CH2:18][CH2:19][CH3:20])=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH2:7][CH2:8]1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 5352426Tin atomHCID 66783328HCID 66783328, compound

Product 1

HCID 24956860HCID 24956860, compound

Reagents, catalysts & solvents 2

HCID 260Hydrogen BromideSolventHCID 6344DichloromethaneSolvent

Procedure

Ex. 44 (1,057 mg, 2.948 mmol) was dissolved in hydrogen bromide/glacial acetic acid (33% HBr, 70 ml). Tin powder (5.250 g, 44.2 mmol) was then added to the mixture in portions at room temperature in the course of 1 h and the mixture was stirred for a further 1 h. The mixture was then diluted with methylene chloride (250 ml). 3 N sodium hydroxide solution (750 ml) was added, while cooling. The mixture was stirred at room temperature for 20 min. After separation of the phases, the aqueous phase was extracted with methylene chloride (3×20 ml). The combined organic extracts were dried over Na2SO4 and then concentrated (976 mg of beige-coloured solid). After separation of this mixture by chromatography [silica gel 60 (100 g); ethyl acetate/methanol 10:1 (550 ml), ethyl acetate/methanol 20:3 (575 ml), ethyl acetate/methanol 5:1 (1,200 ml), ethyl acetate/methanol 3:1 (400 ml)] N,N-dimethyl-1-phenyl-4-(3-propyl-1H-indol-2-yl)cyclohexanamine (less polar diastereoisomer) (318 mg, 30%, m.p.: 177-181° C.) and the more polar diastereoisomer (267 mg, 25%, m.p.: 211-215° C.) were obtained as white and, respectively, beige-coloured solids.

Workup

  1. temperaturewhile cooling
  2. stirringThe mixture was stirred at room temperature for 20 min
  3. customAfter separation of the phases
  4. extractionthe aqueous phase was extracted with methylene chloride (3×20 ml)
  5. dry with materialThe combined organic extracts were dried over Na2SO4
  6. concentrationconcentrated (976 mg of beige-coloured solid)
  7. customAfter separation of this mixture by chromatography [silica gel 60 (100 g); ethyl acetate/methanol 10:1 (550 ml), ethyl acetate/methanol 20:3 (575 ml), ethyl acetate/methanol 5:1 (1,200 ml), ethyl acetate/methanol 3:1 (400 ml)] N,N-dimethyl-1-phenyl-4-(3-propyl-1H-indol-2-yl)cyclohexanamine (less polar diastereoisomer) (318 mg, 30%, m.p.: 177-181° C.)
  8. customthe more polar diastereoisomer (267 mg, 25%, m.p.: 211-215° C.) were obtained as white and, respectively, beige-coloured solids

Sources & evidence

ORD record
ord-70ea54f6668e4ce38992906c544e7463
Source dataset
uspto-grants-2012_03
Patent number
US08138187B2

Reaction notes

Loading…