Acetic Acid → HCID 10298721, compound

HRID 1179052Notes

Reaction equation

HRID 1179052 reaction equation
[CH2:1]([O:8][C:9]1[CH:20]=[C:19]2[C:12]([NH:13][CH:14]=[C:15]2[CH2:16][CH2:17][NH2:18])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:21][N:22]([CH3:36])[C:23]1([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:28][CH2:27][C:26](=O)[CH2:25][CH2:24]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.O>[CH2:1]([O:8][C:9]1[CH:20]=[C:19]2[C:12](=[CH:11][CH:10]=1)[NH:13][CH:14]=[C:15]2[CH2:16][CH2:17][NH:18][CH:26]1[CH2:25][CH2:24][C:23]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)([N:22]([CH3:36])[CH3:21])[CH2:28][CH2:27]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 895762-[5-(Benzyloxy)-1H-indol-3-yl]ethan-1-amineHCID 5049666Sodium triacetoxyborohydrideHCID 114244924-(Dimethylamino)-4-phenylcyclohexan-1-one

Product 1

HCID 10298721HCID 10298721, compoundYield 51.3%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 962WaterSolvent

Procedure

5-Benzyloxytryptamine (440 mg, 1.65 mmol) were dissolved in 1,2-dichloroethane (14 ml) under argon (slightly cloudy solution). After addition of 4-dimethylamino-4-phenylcyclohexanone (359 mg, 1.65 mmol) and glacial acetic acid (189 μl, 3.3 mmol), the mixture was stirred for two hours at RT. Sodium triacetoxyborohydride (462 mg) was then added and the suspension was stirred for four days at RT. For working up, water (15 ml) was added to the reaction mixture. The phases were separated and the aqueous phase was washed with ether (20 ml) and then rendered strongly alkaline with sodium hydroxide solution. The aqueous phase was extracted with ether (2×10 ml) and ethyl acetate (4×10 ml), the combined extracts were dried over sodium sulfate and filtered and the filtrate was concentrated. The crude product obtained (686 mg) was recrystallized from a mixture of ethyl acetate/cyclohexane (35 ml/5 ml). 396 mg N′-[2-(5-benzyloxy-1H-indol-3-yl)-ethyl]-N,N-dimethyl-1-phenyl-cyclohexane-1,4-diamine were obtained as a cis/trans mixture (m.p. 130-134° C.).

Workup

  1. stirringthe suspension was stirred for four days at RT
  2. customThe phases were separated
  3. washthe aqueous phase was washed with ether (20 ml)
  4. extractionThe aqueous phase was extracted with ether (2×10 ml) and ethyl acetate (4×10 ml)
  5. dry with materialthe combined extracts were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated
  8. customThe crude product obtained (686 mg)
  9. customwas recrystallized from a mixture of ethyl acetate/cyclohexane (35 ml/5 ml)

Sources & evidence

ORD record
ord-b8cba4ba6fd5468d9dc74afdab319086
Source dataset
uspto-grants-2007_10
Patent number
US07276518B2

Reaction notes

Loading…