Acetic Acid → HCID 9925137, compound

HRID 1179049Notes

Reaction equation

HRID 1179049 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.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][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 176Acetic AcidHCID 1150TryptamineHCID 5049666Sodium triacetoxyborohydrideHCID 114244924-(Dimethylamino)-4-phenylcyclohexan-1-one

Product 1

HCID 9925137HCID 9925137, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 962WaterSolvent

Procedure

Tryptamine (320 mg) was dissolved in dry 1,2-dichloroethane (10 ml) under argon. After addition of 4-dimethylamino-4-phenylcyclohexanone (435 mg), glacial acetic acid (229 μl) and sodium triacetoxyborohydride (550 mg), the suspension was stirred for 3 days at RT. For working up, water (20 ml) was added to the reaction mixture. The organic phase was separated off and the aqueous phase was extracted once with ether and then rendered strongly alkaline with sodium hydroxide solution. The aqueous phase was milky-cloudy at pH 10. It was extracted with ethyl acetate (4×10 ml), the extracts were combined, dried over sodium sulfate and filtered and the filtrate was concentrated. The crude product obtained (674 mg) was recrystallized twice from ethyl acetate (5 ml). 22 mg of the nonpolar diastereoisomer of N′-[2-(1H-indol-3-yl)-ethyl]-N,N-dimethyl-1-phenyl-cyclohexane-1,4-diamine were obtained (m.p. 134-138° C.).

Workup

  1. customThe organic phase was separated off
  2. extractionthe aqueous phase was extracted once with ether
  3. extractionIt was extracted with ethyl acetate (4×10 ml)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated
  7. customThe crude product obtained (674 mg)
  8. customwas recrystallized twice from ethyl acetate (5 ml)

Sources & evidence

ORD record
ord-6efc315b94fe4fbd9cec5f28cb60fac1
Source dataset
uspto-grants-2007_10
Patent number
US07276518B2

Reaction notes

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