Acetaldehyde → HCID 9951524, compound

HRID 2250132Notes

Reaction equation

HRID 2250132 reaction equation
Cl.Cl.[N:3]1([CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:14]=[C:15]3[C:20](=[CH:21][CH:22]=2)[CH2:19][NH:18][CH2:17][CH2:16]3)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.[CH:23](=O)[CH3:24]>C(Cl)Cl.CO>[CH2:23]([N:18]1[CH2:17][CH2:16][C:15]2[C:20](=[CH:21][CH:22]=[C:13]([O:12][CH2:11][CH2:10][CH2:9][N:3]3[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]3)[CH:14]=2)[CH2:19]1)[CH3:24]

Participants

4

Reactant 2

HCID 177AcetaldehydeHCID 69308514HCID 69308514, compound

Product 1

HCID 9951524HCID 9951524, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

To a 25 mL round-bottom flask is placed 6-(3-Piperidin-1-yl-propoxy)-1,2,3,4-tetrahydro-isoquinoline dihydrochloride (700 mg, 2.01 mol), MP-CNBH3 (2.5 g, 6.05 mmol, 2.42 mmol/g) and DCM/MeOH (9 mL/1 mL). Then, acetaldehyde is added (0.7 mL, 12 mmol) and the reaction is allowed to stir overnight. The reaction is then filtered, washed with DCM/MeOH and concentrated. Column chromatography in 9:1 DCM:MeOH affords 2-ethyl-6-(3-piperidin-1-yl-propoxy)-1,2,3,4-tetrahydro-isoquinoline (493 mg, 71%) of a viscous oil. Mass spec hit M+1, 303; LCMS>95% @ 230 nm and ELSD. Array synthesis followed this general procedure in 4 mL vials to make the following compounds:

Workup

  1. customTo a 25 mL round-bottom flask is placed
  2. filtrationThe reaction is then filtered
  3. washwashed with DCM/MeOH
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4b3c782bafb740559742a9fe9a158b24
Source dataset
uspto-grants-2008_01
Patent number
US07314937B2

Reaction notes

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