Formaldehyde → HCID 10331376, compound

HRID 1789670Notes

Reaction equation

HRID 1789670 reaction equation
[CH2:1]1[C@H:13]2[C@H:4]([N:5]([CH2:14][CH2:15][NH2:16])[C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=3[CH2:12]2)[CH2:3][CH2:2]1.C=O.[C:19](O)(C(F)(F)F)=O>CCO>[CH2:14]1[N:5]2[C:6]3[C:11]([CH2:12][C@@H:13]4[CH2:1][CH2:2][CH2:3][C@H:4]42)=[CH:10][CH:9]=[CH:8][C:7]=3[CH2:19][NH:16][CH2:15]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 6422Trifluoroacetic acidHCID 86590897HCID 86590897, compound

Product 1

HCID 10331376HCID 10331376, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A flask containing Cis 2-(1,2,3,3a,9,9a-Hexahydro-cyclopenta[b]quinolin-4-yl)-ethylamine (0.18 g, 0.84 mmol) and 0.07 ml of 37% aqueous formaldehyde in 2 ml of EtOH was treated with TFA (0.07 mL, 0.92 mmol) at room temperature for 1 hr. The mixture was concentrated under reduced pressure, and the residue was taken up in dichloromethane, washed with 1 N NaOH (15 mL), Brine (15 mL) and then dried with MgSO4. Evaporation and flash chromatography (10% 2N NH3 in ethanol/dichloromethane) afforded the title compound, which was converted to the HCl salt to give a brown solid (0.19 mg, 85%): The same step 5 procedure was used to prepare the trans isomer except that Trans 2-(1,2,3,3a,9,9a-Hexahydro-cyclopenta[b]quinolin-4-yl)-ethylamine was used instead of the cis isomer.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. washwashed with 1 N NaOH (15 mL), Brine (15 mL)
  3. dry with materialdried with MgSO4
  4. customEvaporation and flash chromatography (10% 2N NH3 in ethanol/dichloromethane)

Sources & evidence

ORD record
ord-095e3ffa08bd49d9aef030a37ce27fc7
Source dataset
uspto-grants-2006_07
Patent number
US07071185B2

Reaction notes

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