1,2-Dichloroethane → HCID 9925137, compound

HRID 1179071Notes

Reaction equation

HRID 1179071 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.[CH3:13][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.ClCCCl.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>O1CCCC1.C(O)(=O)C>[NH:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:4]([CH2:3][CH2:2][NH:1][CH:18]2[CH2:17][CH2:16][C:15]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)([N:14]([CH3:28])[CH3:13])[CH2:20][CH2:19]2)=[CH:5]1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 1150TryptamineHCID 5049666Sodium triacetoxyborohydrideHCID 114244924-(Dimethylamino)-4-phenylcyclohexan-1-one

Product 1

HCID 9925137HCID 9925137, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.12 g tryptamine and 1.52 g 4-dimethylamino-4-phenylcyclohexanone were dissolved in dry tetrahydrofuran (12 ml) and 1,2-dichloroethane (40 ml) under argon. Glacial acetic acid (801 μl) and 1.92 g sodium triacetoxyborohydride were added to this mixture and the mixture was stirred for four days at RT. For working up, the reaction mixture was concentrated and the residue was taken up in water (20 ml), two molar hydrochloric acid (5 ml) and ether (35 ml). The aqueous phase was separated off, washed with ether (2×15 ml), adjusted to pH 11 with sodium hydroxide solution and extracted with ethyl acetate (3×20 ml). The combined extracts were dried over sodium sulfate and filtered and the filtrate was concentrated. The beige-brown residue obtained (2.0 g) was chromatographed over silica gel with methanol which contained 0.75 vol. % triethylamine. 553 mg of the nonpolar diastereomer of N′-[2-(1H-indol-3-yl)-ethyl]-N,N-dimethyl-1-phenyl-cyclohexane-1,4-diamine were obtained (m.p. 175-178° C.), from which the corresponding dihydrochloride was obtained with chlorotrimethylsilane in 2-butanone/acetone (20 ml/50 ml) (600 mg; m.p. 216-218° C.).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. customThe aqueous phase was separated off
  3. washwashed with ether (2×15 ml)
  4. extractionextracted with ethyl acetate (3×20 ml)
  5. dry with materialThe combined extracts were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated
  8. customThe beige-brown residue obtained (2.0 g)
  9. customwas chromatographed over silica gel with methanol which

Sources & evidence

ORD record
ord-3cffd1c0c2a54d6882a53d4cc365dc4a
Source dataset
uspto-grants-2007_10
Patent number
US07276518B2

Reaction notes

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