Acetic Acid → HCID 9956432, compound

HRID 890611Notes

Reaction equation

HRID 890611 reaction equation
C(O)(=O)C.[CH3:5][N:6]([CH3:20])[C:7]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[CH2:12][CH2:11][C:10](=O)[CH2:9][CH2:8]1.[NH2:21][CH2:22][CH2:23][C:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[NH:26][CH:25]=1>O1CCCC1.ClCCCl>[NH:26]1[C:27]2[C:32](=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:24]([CH2:23][CH2:22][NH:21][CH:10]2[CH2:11][CH2:12][C:7]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=3)([N:6]([CH3:20])[CH3:5])[CH2:8][CH2:9]2)=[CH:25]1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 1150TryptamineHCID 11276004HCID 11276004, compound

Product 1

HCID 9956432HCID 9956432, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Acetic acid (0.448 ml) was added to a solution of 4-dimethylamino-4-pyridin-2-yl cyclohexanone (873 mg) and tryptamine (640 mg) in dry tetrahydrofuran (40 ml) and anhydrous 1,2-dichloroethane (10 ml) and stirred for 15 min. Following addition of sodium triacetoxyboron hydride (1.2 g) the reaction mixture was stirred for three days under argon at room temperature. To recover the product the solvent was removed in vacuo, the residue taken up in 1N sodium hydroxide solution (40 ml) and diethyl ether (40 ml), the phases separated, the aqueous phase extracted with diethyl ether (2×30 ml), the organic phases combined, dried and concentrated to low volume. The resulting raw product was separated by column chromatography on silica gel with methanol and methanol/ammonia (100:1). The non-polar diastereoisomer of N′-[2-(1H-indol-3-yl)ethyl]-N,N-dimethyl-1-pyridin-2-yl cyclohexane-1,4-diamine was obtained as a white solid (617 mg; mp 150–152° C.).

Workup

  1. stirringwas stirred for three days under argon at room temperature
  2. customTo recover the product the solvent
  3. customwas removed in vacuo
  4. customdiethyl ether (40 ml), the phases separated
  5. extractionthe aqueous phase extracted with diethyl ether (2×30 ml)
  6. customdried
  7. concentrationconcentrated to low volume
  8. customThe resulting raw product was separated by column chromatography on silica gel with methanol and methanol/ammonia (100:1)

Sources & evidence

ORD record
ord-5aa869d2d8304ce58b4825eee5622084
Source dataset
uspto-grants-2006_02
Patent number
US06998409B2

Reaction notes

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