1,2-Dichloroethane → HCID 69337485, compound

HRID 1179076Notes

Reaction equation

HRID 1179076 reaction equation
[CH2:1]([O:8][C:9]1[CH:20]=[CH:19][CH:18]=[C:17]2[C:10]=1[NH:11][CH:12]=[C:13]2[CH2:14][CH2:15][NH2:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1COCC1.[CH3:26][N:27]([CH3:41])[C:28]1([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:33][CH2:32][C:31](=O)[CH2:30][CH2:29]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl:56]CCCl>C(O)(=O)C>[ClH:56].[ClH:56].[CH2:1]([O:8][C:9]1[CH:20]=[CH:19][CH:18]=[C:17]2[C:10]=1[NH:11][CH:12]=[C:13]2[CH2:14][CH2:15][NH:16][CH:31]1[CH2:30][CH2:29][C:28]([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)([N:27]([CH3:41])[CH3:26])[CH2:33][CH2:32]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 8028TetrahydrofuranHCID 2608067-BenzyloxytryptamineHCID 5049666Sodium triacetoxyborohydrideHCID 114244924-(Dimethylamino)-4-phenylcyclohexan-1-one

Product 1

HCID 69337485HCID 69337485, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

7-Benzyloxytryptamine (200 mg) was dissolved in dry 1,2-dichloroethane (10 ml) and THF (10 ml) under argon. After addition of 4-dimethylamino-4-phenylcyclohexanone (180 mg) and glacial acetic acid (43 μl), the mixture was stirred for one hour at RT and then sodium triacetoxyborohydride (248 mg) was added thereto. The reaction mixture was stirred for three days at RT. For working up, the mixture was concentrated, the residue was dissolved in water (15 ml), 2M HCl (2 ml) and diethyl ether (20 ml), the organic phase was separated off, and the aqueous phase was washed with diethyl ether (2×15 ml), brought to pH 11 with 1M NaOH and extracted with ethyl acetate (4×10 ml). The combined ethyl acetate extracts were dried and concentrated, and the residue obtained (351 mg) was purified by flash chromatography (45 g silica gel 60, eluant: MeOH/NEt3 (99:1)). The nonpolar diastereomer (188 mg) was dissolved in 2-butanone/acetone (6 ml/6 ml) while warm and converted with chlorotrimethylsilane (147 μl) into the corresponding dihydrochloride (white solid; 176 mg; m.p. 162-166° C.).

Workup

  1. stirringThe reaction mixture was stirred for three days at RT
  2. concentrationthe mixture was concentrated
  3. dissolutionthe residue was dissolved in water (15 ml)
  4. custom2M HCl (2 ml) and diethyl ether (20 ml), the organic phase was separated off
  5. washthe aqueous phase was washed with diethyl ether (2×15 ml)
  6. extractionextracted with ethyl acetate (4×10 ml)
  7. dry with materialThe combined ethyl acetate extracts were dried
  8. concentrationconcentrated
  9. customthe residue obtained (351 mg)
  10. customwas purified by flash chromatography (45 g silica gel 60, eluant: MeOH/NEt3 (99:1))
  11. dissolutionThe nonpolar diastereomer (188 mg) was dissolved in 2-butanone/acetone (6 ml/6 ml)
  12. temperaturewhile warm

Sources & evidence

ORD record
ord-cbd2f3d65e2c47ba8ba85fbba73a537b
Source dataset
uspto-grants-2007_10
Patent number
US07276518B2

Reaction notes

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