Acetic Acid → HCID 9924406, compound

HRID 1179066Notes

Reaction equation

HRID 1179066 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][NH2:11])=[CH:2]1.[CH3:12][N:13]([CH3:27])[C:14]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:19][CH2:18][C:17](=O)[CH2:16][CH2:15]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>O1CCCC1.ClCCCl>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][NH:11][CH:17]2[CH2:16][CH2:15][C:14]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)([N:13]([CH3:27])[CH3:12])[CH2:19][CH2:18]2)=[CH:2]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 4721071H-Indol-3-YlmethanamineHCID 5049666Sodium triacetoxyborohydrideHCID 114244924-(Dimethylamino)-4-phenylcyclohexan-1-one

Product 1

HCID 9924406HCID 9924406, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

970 mg C-(1H-Indol-3-yl)methylamine and 1.44 mg 4-dimethylamino-4-phenyl-cyclohexanone were dissolved in dry tetrahydrofuran (15 ml) and 1,2-dichloroethane (50 ml) under argon. Glacial acetic acid (13.2 mmol) and 1.82 g sodium triacetoxyborohydride were added to this mixture and the mixture was stirred for 72 hours at RT. For working up, the reaction mixture was concentrated, water (20 ml) and ether (30 ml) were added to the residue and the mixture was stirred vigorously. The aqueous phase was separated off, washed with ether (2×15 ml), adjusted to pH 11 with five molar sodium hydroxide solution and extracted with ethyl acetate (4×25 ml). The combined extracts were dried over sodium sulfate and filtered and the filtrate was concentrated. The crude product (2.11 g) was chromatographed over silica gel with methanol/triethylamine (199:1). 465 mg of the nonpolar diastereomer of N′-(1H-indol-3-ylmethyl)-N,N-dimethyl-1-phenyl-cyclohexane-1,4-diamine were obtained (m.p. 182-184° C.), from which the corresponding dihydrochloride was precipitated with chlorotrimethylsilane (443 μl) in 2-butanone/acetone (20 ml/50 ml) (498 mg; m.p. 164-168° C.).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. additionwater (20 ml) and ether (30 ml) were added to the residue
  3. stirringthe mixture was stirred vigorously
  4. customThe aqueous phase was separated off
  5. washwashed with ether (2×15 ml)
  6. extractionextracted with ethyl acetate (4×25 ml)
  7. dry with materialThe combined extracts were dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationthe filtrate was concentrated
  10. customThe crude product (2.11 g) was chromatographed over silica gel with methanol/triethylamine (199:1)

Sources & evidence

ORD record
ord-9ee5d885e9cb4e1babdce40498e93294
Source dataset
uspto-grants-2007_10
Patent number
US07276518B2

Reaction notes

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