1,2-Dichloroethane → n'-[2-(1h-Indol-3-yl)-1-methyl-ethyl]-n,n-dimethyl-1-thiophen-2-yl-cyclohexane-1,4-diamine dihydrochloride

HRID 1179075Notes

Reaction equation

HRID 1179075 reaction equation
[CH3:1][CH:2]([NH2:13])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.[CH3:14][N:15]([CH3:28])[C:16]1([C:23]2[S:24][CH:25]=[CH:26][CH:27]=2)[CH2:21][CH2:20][C:19](=O)[CH2:18][CH2:17]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl:47]CCCl>O>[ClH:47].[ClH:47].[NH:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:4]([CH2:3][CH:2]([NH:13][CH:19]2[CH2:20][CH2:21][C:16]([C:23]3[S:24][CH:25]=[CH:26][CH:27]=3)([N:15]([CH3:28])[CH3:14])[CH2:17][CH2:18]2)[CH3:1])=[CH:5]1

Participants

7

Reactant 5

HCID 111,2-Dichloroethane2×HCID 176Acetic AcidHCID 9287(+-)-alpha-MethyltryptamineHCID 5049666Sodium triacetoxyborohydrideHCID 12595637HCID 12595637, compound

Product 1

HCID 69337413n'-[2-(1h-Indol-3-yl)-1-methyl-ethyl]-n,n-dimethyl-1-thiophen-2-yl-cyclohexane-1,4-diamine dihydrochloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

DL-α-Methyltryptamine (N′-[2-(1H-indol-3-yl)-1-methylethyl]-N,N-dimethyl-1-thiophen-2-yl-cyclohexane-1,4-diamine, 348 mg) was dissolved in dry 1,2-dichloroethane (20 ml) under argon. After addition of 4-dimethylamino-4-thiophen-2-yl-cyclohexanone (447 mg) and glacial acetic acid (114 μl), a bulky precipitate formed. The suspension was stirred for one hour at RT. Sodium triacetoxyborohydride (660 mg) was then added and the reaction mixture was stirred for two days at RT. For working up, the mixture was diluted with 1,2-dichloroethane (10 ml) and water (15 ml), the organic phase was separated off, and the aqueous phase was again extracted with 1,2-dichloroethane (2×5 ml), rendered alkaline with 5M NaOH and extracted with ethyl acetate (4×15 ml). The combined organic phases were dried, concentrated and purified by flash chromatography (50 g silica gel 60, eluant: methanol/NEt3 (99:1)). The nonpolar diastereomer (202 mg, m.p. 158-161° C.) was dissolved in 2-butanone (5 ml) and converted with chlorotrimethylsilane (202 μl) into the corresponding dihydrochloride (white solid, 207 mg; m.p. 162-165° C.).

Workup

  1. customa bulky precipitate formed
  2. stirringthe reaction mixture was stirred for two days at RT
  3. customthe organic phase was separated off
  4. extractionthe aqueous phase was again extracted with 1,2-dichloroethane (2×5 ml)
  5. extractionextracted with ethyl acetate (4×15 ml)
  6. customThe combined organic phases were dried
  7. concentrationconcentrated
  8. custompurified by flash chromatography (50 g silica gel 60, eluant: methanol/NEt3 (99:1))
  9. dissolutionThe nonpolar diastereomer (202 mg, m.p. 158-161° C.) was dissolved in 2-butanone (5 ml)

Sources & evidence

ORD record
ord-8ddc176c159c49e1b51afc21d672e0b1
Source dataset
uspto-grants-2007_10
Patent number
US07276518B2

Reaction notes

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