Acetic Acid → HCID 9923765, compound

HRID 1179050Notes

Reaction equation

HRID 1179050 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][CH2:6][CH2:5]2.[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>[CH2:7]1[C:8]2[C:4](=[CH:3][C:2]([NH:1][CH:16]3[CH2:15][CH2:14][C:13]([C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=4)([N:12]([CH3:26])[CH3:11])[CH2:18][CH2:17]3)=[CH:10][CH:9]=2)[CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 90496Indan-5-amineHCID 5049666Sodium triacetoxyborohydrideHCID 114244924-(Dimethylamino)-4-phenylcyclohexan-1-one

Product 1

HCID 9923765HCID 9923765, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

5-Aminoindane (266 mg) and 4-dimethylamino-4-phenylcyclohexanone (434 mg) were dissolved in dry 1,2-dichloroethane (10 ml) under argon. Glacial acetic acid (2 mmol) and sodium triacetoxyborohydride (600 mg) were added and the mixture was stirred for 24 hours at RT. For working up, the reaction 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 (4×20 ml). The combined extracts were dried over sodium sulfate and filtered and the filtrate was concentrated. The crude product obtained was chromatographed over silica gel with ethyl acetate/ethanol (1:1). 270 mg of the nonpolar diastereoisomer of N′-indan-5-yl-N,N-dimethyl-1-phenyl-cyclohexane-1,4-diamine were obtained as a white solid (m.p. 162-164° C.).

Workup

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

Sources & evidence

ORD record
ord-104698547f6e4aff82b503985fb5178e
Source dataset
uspto-grants-2007_10
Patent number
US07276518B2

Reaction notes

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