Acetyl chloride → 1-(7-(3-(piperidin-1-yl)propoxy)-3,4-dihydroisoquinolin-2(1H)-yl)ethanone

HRID 2250119Notes

Reaction equation

HRID 2250119 reaction equation
Cl.Cl.[N:3]1([CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:22]=[C:21]3[C:16]([CH2:17][CH2:18][NH:19][CH2:20]3)=[CH:15][CH:14]=2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.CCN(CC)CC.[C:30](Cl)(=[O:32])[CH3:31]>C(Cl)Cl>[N:3]1([CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:22]=[C:21]3[C:16]([CH2:17][CH2:18][N:19]([C:30](=[O:32])[CH3:31])[CH2:20]3)=[CH:15][CH:14]=2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 69311509HCID 69311509, compound

Product 1

HCID 444126991-(7-(3-(piperidin-1-yl)propoxy)-3,4-dihydroisoquinolin-2(1H)-yl)ethanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 5 mL CH2Cl2 solution of 7-(3-piperidin-1-yl-propoxy)-1,2,3,4-tetrahydro-isoquinoline dihydrochloride (175 mg, 0.5 mmol) and NEt3 (0.25 mL, 1.7 mmol) is stirred under N2, a 1 mL CH2Cl2 solution of acetyl chloride (0.043 mL, 0.6 mmol) is added, and reaction is stirred at room temp. for 5-6 hours. Reaction mixture is quenched with MeOH, concentrated and the residue is purified by chromatography (SCX-MeOH wash, elute 2M NH3/MeOH; then (SiO2; 0-10% MeOH/CH2Cl2/1% NH4OH gradient) to give the product (90 mg, 58% yld). MS(ES+)317.1(M+H)+

Workup

  1. customreaction
  2. customReaction mixture
  3. customis quenched with MeOH
  4. concentrationconcentrated
  5. customthe residue is purified by chromatography (SCX-MeOH
  6. washwash
  7. washelute 2M NH3/MeOH
  8. customthen (SiO2; 0-10% MeOH/CH2Cl2/1% NH4OH gradient) to give the product (90 mg, 58% yld)

Sources & evidence

ORD record
ord-818a83ff485a4f6e80c9392517763624
Source dataset
uspto-grants-2008_01
Patent number
US07314937B2

Reaction notes

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