1,2-Dichloroethane → HCID 69337727, compound

HRID 1179059Notes

Reaction equation

HRID 1179059 reaction equation
S1C=[C:4]([NH:6]CC)[C:3]2[CH:9]=[CH:10]C=CC1=2.[CH3:13][N:14]([CH3:28])[C:15]1([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:20][CH2:19][C:18](=O)[CH2:17][CH2:16]1.[S:29]([O-])([O-])(=O)=O.[Na+].[Na+].C(O[BH-](O[C:46](=O)[CH3:47])OC(=O)C)(=O)C.[Na+].[C:50](O)(=O)[CH3:51].C(=O)([O-])[O-].[Na+].[Na+].[ClH:60].[Cl:61][CH2:62][CH2:63]Cl>CC(=O)CC.C(OCC)(=O)C.O>[ClH:61].[ClH:60].[S:29]1[CH:10]=[C:9]([CH2:3][CH2:4][NH:6][CH:18]2[CH2:19][CH2:20][C:15]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)([N:14]([CH3:28])[CH3:13])[CH2:16][CH2:17]2)[C:62]2[CH:63]=[CH:50][CH:51]=[CH:47][C:46]1=2

Participants

12

Reactant 8

HCID 111,2-DichloroethaneHCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 24436Sodium SulfateHCID 5049666Sodium triacetoxyborohydrideHCID 114244924-(Dimethylamino)-4-phenylcyclohexan-1-oneHCID 66641394HCID 66641394, compound

Product 1

HCID 69337727HCID 69337727, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6569Methyl Ethyl KetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Benzo[b]thiophen-3-yl-ethylamine (289 mg, 1.6 mmol) was dissolved in dry 1,2-dichloroethane (10 ml) under argon and, after addition of 4-dimethylamino-4-phenylcyclohexanone (354 mg, 1.6 mmol) and sodium sulfate (2 g), the mixture was stirred for one hour at RT. Sodium triacetoxyborohydride (440 mg, 2.0 mmol) was then added to the reaction mixture in one portion. After 3 days, glacial acetic acid (4 mmol) was subsequently added and the mixture was stirred for a further 24 hours at RT. For working up, water (20 ml) was added and the reaction mixture was filtered with suction. The solid obtained was dissolved with two molar sodium carbonate solution and ethyl acetate. The organic phase was separated off, dried over sodium sulfate and filtered and the filtrate concentrated. The solid but tacky residue obtained (213 mg) was dissolved in 2-butanone (5 ml), and ethanolic HCl (500 μl, 1.5 mmol) was added at RT. After two hours, the solution was concentrated to dryness and the residue was suspended in diethyl ether (5 ml), filtered off with suction and rinsed with diethyl ether (3×3 ml). A mixture of cis- and trans-N′-(2-benzo[b]thiophen-3-yl-ethyl)-N,N-dimethyl-1-phenyl-cyclohexane-1,4-diamine dihydrochloride (217 mg, m.p. 164-167° C.) was obtained as a beige-brown solid.

Workup

  1. waitAfter 3 days
  2. stirringthe mixture was stirred for a further 24 hours at RT
  3. filtrationthe reaction mixture was filtered with suction
  4. customThe solid obtained
  5. customThe organic phase was separated off
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationthe filtrate concentrated
  9. customThe solid but tacky residue obtained (213 mg)
  10. waitAfter two hours
  11. concentrationthe solution was concentrated to dryness
  12. filtrationfiltered off with suction
  13. washrinsed with diethyl ether (3×3 ml)
  14. additionA mixture of cis- and trans-N′-(2-benzo[b]thiophen-3-yl-ethyl)-N,N-dimethyl-1-phenyl-cyclohexane-1,4-diamine dihydrochloride (217 mg, m.p. 164-167° C.)
  15. customwas obtained as a beige-brown solid

Sources & evidence

ORD record
ord-828716d8595d4e6786fb34468c311022
Source dataset
uspto-grants-2007_10
Patent number
US07276518B2

Reaction notes

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