Acetic Acid → HCID 10110019, compound

HRID 1179051Notes

Reaction equation

HRID 1179051 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]([CH3:29])[C:16]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=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+]>ClCCCl.O>[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[CH2:18][CH2:17][C:16]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)([N:15]([CH3:29])[CH3:14])[CH2:21][CH2:20]2)[CH3:1])=[CH:5]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 9287(+-)-alpha-MethyltryptamineHCID 5049666Sodium triacetoxyborohydrideHCID 114244924-(Dimethylamino)-4-phenylcyclohexan-1-one

Product 1

HCID 10110019HCID 10110019, compoundYield 17%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 962WaterSolvent

Procedure

DL-α-Methyltryptamine (348 mg, 2 mmol) was dissolved in dry 1,2-dichloroethane (10 ml) under argon. After addition of 4-dimethylamino-4-phenylcyclohexanone (435 mg) and glacial acetic acid (229 μl), the mixture was stirred for one hour at RT. Sodium triacetoxyborohydride (550 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 clear phases were separated and the aqueous phase was washed with ether (10 ml) and then rendered strongly alkaline with sodium hydroxide solution. The aqueous phase was extracted with ethyl acetate (4×10 ml), the combined extracts were dried over sodium sulfate and filtered and the filtrate was concentrated. The crude product obtained (723 mg) was recrystallized twice from a mixture of ethyl acetate/cyclohexane (2 ml/6 ml). A fraction of the nonpolar diastereoisomer of N′-[2-(1H-indol-3-yl)-1-methyl-ethyl]-N,N-dimethyl-1-phenyl-cyclohexane-1,4-diamine (128 mg, m.p. 155-162° C.) was obtained.

Workup

  1. stirringthe suspension was stirred for four days at RT
  2. customThe clear phases were separated
  3. washthe aqueous phase was washed with ether (10 ml)
  4. extractionThe aqueous phase was extracted with 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 (723 mg)
  9. customwas recrystallized twice from a mixture of ethyl acetate/cyclohexane (2 ml/6 ml)

Sources & evidence

ORD record
ord-f98cf71803a64f4aac4bc9c403bfe4b8
Source dataset
uspto-grants-2007_10
Patent number
US07276518B2

Reaction notes

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