Acetic Acid → HCID 9858911, compound

HRID 1179047Notes

Reaction equation

HRID 1179047 reaction equation
[NH2:1][CH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3]1.[CH3:11][N:12]([CH3:26])[C:13]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:18][CH2:17][C:16](=O)[CH2:15][CH2:14]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C1COCC1>[CH:2]1([NH:1][CH:16]2[CH2:15][CH2:14][C:13]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)([N:12]([CH3:26])[CH3:11])[CH2:18][CH2:17]2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 123445(+-)-1-AminoindanHCID 5049666Sodium triacetoxyborohydrideHCID 114244924-(Dimethylamino)-4-phenylcyclohexan-1-one

Product 1

HCID 9858911HCID 9858911, compoundYield 29.9%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

266 mg 1-aminoindane and 434 mg 4-dimethylamino-4-phenyl-cyclohexanone were dissolved in dry 1,2-dichloroethane (10 ml) and THF (10 ml) under argon. Glacial acetic acid (2 mmol) and sodium triacetoxyborohydride (600 mg) were added to this mixture and the mixture was stirred for 24 hours at RT. For working up, the mixture was concentrated and the residue was adjusted to pH 11 with five molar sodium hydroxide solution. The alkaline phase was diluted with water (10 ml) and extracted with ethyl acetate (5×20 ml). The combined extracts were dried over sodium sulfate and filtered and the filtrate was concentrated. The crude product was chromatographed over silica gel with ethyl acetate/ethanol (1:1). 200 mg N′-indan-1-yl-N,N-dimethyl-1-phenyl-cyclohexane-1,4-diamine were obtained as a white solid (m.p. 99-101° C.).

Workup

  1. concentrationthe mixture was concentrated
  2. additionThe alkaline phase was diluted with water (10 ml)
  3. extractionextracted with ethyl acetate (5×20 ml)
  4. dry with materialThe combined extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated
  7. customThe crude product was chromatographed over silica gel with ethyl acetate/ethanol (1:1)

Sources & evidence

ORD record
ord-3945a21421a64bb69152e614297d36b6
Source dataset
uspto-grants-2007_10
Patent number
US07276518B2

Reaction notes

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