Boron Trichloride → {4-[(7-Hydroxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-propyl-amino]-piperidin-1-yl}-morpholin-4-yl-methanone

HRID 393213Notes

Reaction equation

HRID 393213 reaction equation
C[O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH:9]([N:13]([CH2:28][CH2:29][CH3:30])[CH:14]3[CH2:19][CH2:18][N:17]([C:20]([N:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)=[O:21])[CH2:16][CH2:15]3)[CH2:10]2)=[CH:5][CH:4]=1.B(Cl)(Cl)Cl>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl>[OH:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH:9]([N:13]([CH2:28][CH2:29][CH3:30])[CH:14]3[CH2:15][CH2:16][N:17]([C:20]([N:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)=[O:21])[CH2:18][CH2:19]3)[CH2:10]2)=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 25135Boron TrichlorideHCID 10216398HCID 10216398, compound

Product 1

HCID 22649552{4-[(7-Hydroxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-propyl-amino]-piperidin-1-yl}-morpholin-4-yl-methanoneYield 44.3%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a −78° C. solution of {4-[(7-methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-propyl-amino]-piperidin-1-yl}-morpholin-4-yl-methanone (300 mg, 0.72 mmol) and tetrabutylammonium iodide (292 mg, 0.79mmol) in dichloromethane (20 mL) under an inert atmosphere was added boron trichloride (1M, 2.5 mL, 2.5 mmol) dropwise. The reaction was warmed to room temperature and stirred for 2.5 h. The reaction was quenched by slow addition of water and the organic layer separated and dried (MgSO4). This was concentrated onto silica (1.5 g) and placed on top of a flash column. Chromatography eluting with 30% acetone in hexanes afforded {4-[(7-hydroxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-propyl-amino]-piperidin-1-yl}-morpholin-4-yl-methanone (128 mg).

Workup

  1. customThe reaction was quenched by slow addition of water
  2. customthe organic layer separated
  3. dry with materialdried (MgSO4)
  4. concentrationThis was concentrated onto silica (1.5 g)
  5. washChromatography eluting with 30% acetone in hexanes

Sources & evidence

ORD record
ord-721952a74125458591d1240994bab434
Source dataset
uspto-grants-2004_10
Patent number
US06806278B2

Reaction notes

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