Acetic Acid → HCID 69337355, compound

HRID 1179080Notes

Reaction equation

HRID 1179080 reaction equation
[CH2:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH2:4][CH2:3][NH:2]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.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[ClH:48].C1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl>C1COCC1.ClCCCl.CC(=O)CC.C(O)C>[ClH:48].[ClH:48].[CH3:14][N:15]([CH3:29])[C:16]1([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:17][CH2:18][CH:19]([N:2]2[CH2:3][CH2:4][C:5]3[C:6]4[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=4)[NH:12][C:13]=3[CH2:1]2)[CH2:20][CH2:21]1

Participants

11

Reactant 6

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 107838Tetrahydro-beta-carbolineHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 5049666Sodium triacetoxyborohydrideHCID 114244924-(Dimethylamino)-4-phenylcyclohexan-1-one

Product 1

HCID 69337355HCID 69337355, compound

Reagents, catalysts & solvents 4

HCID 111,2-DichloroethaneSolventHCID 702EthanolSolventHCID 6569Methyl Ethyl KetoneSolventHCID 8028TetrahydrofuranSolvent

Procedure

2,3,4,9-Tetrahydro-1H-β-carboline (345 mg) and 4-dimethylamino-4-phenylcyclohexanone (435 mg) were dissolved in a mixture of THF (10 ml) and 1,2-dichloroethane (15 ml) under argon, and acetic acid (120 mg, 2 mmol.) was added thereto. After 15 minutes, NaBH(OAc)3 (600 mg) was added, stirring was carried out for 68 hours, the reaction mixture was concentrated and the residue was taken up in 1N hydrochloric acid (20 ml) and washed with ether (2×20 ml). The aqueous solution was rendered alkaline with 1M NaOH (30 ml) and extracted with ether (3×30 ml). After drying and concentration of the combined extracts, a semi-solid crude product was obtained which, after separation by column chromatography with methanol/NH3 (500:3), yielded the nonpolar diastereomer (334 mg, m.p. 147-150° C.) which, dissolved with heating in 2-butanone (20 ml) and ethanol (10 ml), was converted with 3.3M ethanolic hydrochloric acid (0.8 ml) into the corresponding dihydrochloride (335 mg; 264-269° C.).

Workup

  1. waitwas carried out for 68 hours
  2. concentrationthe reaction mixture was concentrated
  3. washwashed with ether (2×20 ml)
  4. extractionextracted with ether (3×30 ml)
  5. customAfter drying
  6. customconcentration of the combined extracts, a semi-solid crude product was obtained which
  7. customafter separation by column chromatography with methanol/NH3 (500:3)
  8. customyielded the nonpolar diastereomer (334 mg, m.p. 147-150° C.) which
  9. dissolutiondissolved

Sources & evidence

ORD record
ord-19c1d4ffab3246989c14b1efd16e453b
Source dataset
uspto-grants-2007_10
Patent number
US07276518B2

Reaction notes

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