Triethylamine → HCID 14392041, compound

HRID 1905564Notes

Reaction equation

HRID 1905564 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2([C:18]#[N:19])[CH2:16][CH2:15][C:14](=O)[CH2:13][CH2:12]2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C(N(CC)CC)C.[ClH:27].[NH2:28][CH:29]1[CH2:37][C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH2:30]1.C([BH3-])#N.[Na+]>C(O)C>[ClH:27].[CH2:30]1[C:31]2[C:36](=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:37][CH:29]1[NH:28][CH:14]1[CH2:15][CH2:16][C:11]([C:5]2[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=2)([C:18]#[N:19])[CH2:12][CH2:13]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 1227642-Aminoindan hydrochlorideHCID 749913Cyclohexanecarbonitrile, 1-(3,4-dimethoxyphenyl)-4-oxo-HCID 5003444Sodium cyanoborohydride

Product 1

HCID 14392041HCID 14392041, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-(3,4-dimethoxyphenyl)-4-cyanocyclohexanone (0.71 g, 2.74 mmol), triethylamine (0.38 ml, 2.74 mmol), 2-amino-2,3-dihydro-1H-inden hydrochloride (0.46 g, 2.74 mmol) and sodium cyanoborohydride (0.17 g, 2.7 mmol) in 10 ml ethanol was stirred at 25° C. for 3 days, filtered and the volatiles were removed in vacuo. The residue was diluted with ethyl acetate, washed with water, 1N NaOH and brine and dried (MgSO4). The volatiles were removed in vacuo. The residue was treated with ethyl acetate and anhydrous HCl. The volatiles were removed in vacuo. Recrystallization of the residue with aqueous ethanol gave the product, m.p. >250° C. ##STR20##

Workup

  1. filtrationfiltered
  2. customthe volatiles were removed in vacuo
  3. additionThe residue was diluted with ethyl acetate
  4. washwashed with water, 1N NaOH and brine
  5. dry with materialdried (MgSO4)
  6. customThe volatiles were removed in vacuo
  7. additionThe residue was treated with ethyl acetate and anhydrous HCl
  8. customThe volatiles were removed in vacuo
  9. customRecrystallization of the residue with aqueous ethanol
  10. customgave the product, m.p. >250° C.

Sources & evidence

ORD record
ord-0c1e41ac42ea49f680ba0f95b447e24a
Source dataset
uspto-grants-1989_06
Patent number
US04843081

Reaction notes

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