Acetic Acid → HCID 86752860, compound

HRID 965243Notes

Reaction equation

HRID 965243 reaction equation
N[C@H:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C@H:3]1[O:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([Cl:19])[CH:13]=1.C=O.[C:22]([BH3-])#[N:23].[Na+].[C:26](O)(=O)C>C(#N)C.C(OCC)C>[ClH:18].[Cl:19][C:14]1[CH:13]=[C:12]([CH:17]=[CH:16][C:15]=1[Cl:18])[O:11][C@@H:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:10][C@@H:2]1[N:23]([CH3:22])[CH3:26]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 86752859HCID 86752859, compound

Product 1

HCID 86752860HCID 86752860, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of (±) cis 2-amino-1-(3,4dichlorophenoxy)indane (0.88 g, 3.0 mmol) in acetonitrile (40 ml) was treated with formaldehyde (2 ml of a 37% aqueous solution, 26 mmol) followed by sodium cyanoborohydride (0.38 g, 6.0 mmol). The mixture was stirred at room temperature for 6 days while maintaining the pH at 5-7 by the addition of glacial acetic acid. The reaction mixture was diluted with diethyl ether and washed with 1M sodium hydroxide followed by brine. The organic layer was dried over Na2 SO4 and concentrated in vacuo. Passage through a short column of neutral alumina eluting with 0.5-1% ethanol in chloroform afforded a colourless oil which was converted into the hydrochloride salt and recrystallised to give the title compound as a colourless solid (0.6 g), m.p. 219°-220° C. (from methanol/ethyl acetate/diethyl ether).

Workup

  1. temperaturewhile maintaining the pH at 5-7
  2. washwashed with 1M sodium hydroxide
  3. customThe organic layer was dried over Na2 SO4
  4. concentrationconcentrated in vacuo
  5. customPassage through a short column of neutral alumina eluting with 0.5-1% ethanol in chloroform afforded a colourless oil which
  6. customrecrystallised

Sources & evidence

ORD record
ord-d0ab876c30ba41f28e80d2b8a4302b06
Source dataset
uspto-grants-1998_06
Patent number
US05773463

Reaction notes

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