Phosphorus tribromide → 1'-[4-(Bromomethyl)benzyl]spiro[indene-1,4'-piperidine]

HRID 390394Notes

Reaction equation

HRID 390394 reaction equation
[N:1]1([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22]O)=[CH:18][CH:17]=2)[CH2:6][CH2:5][C:4]2([C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH:8]=[CH:7]2)[CH2:3][CH2:2]1.P(Br)(Br)[Br:25]>C(Cl)Cl.O>[Br:25][CH2:22][C:19]1[CH:20]=[CH:21][C:16]([CH2:15][N:1]2[CH2:6][CH2:5][C:4]3([C:14]4[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=4)[CH:8]=[CH:7]3)[CH2:3][CH2:2]2)=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 24614Phosphorus tribromideHCID 58230582Benzenemethanol, 4-(spiro[1H-indene-1,4'-piperidin]-1'-ylmethyl)-

Product 1

HCID 670871851'-[4-(Bromomethyl)benzyl]spiro[indene-1,4'-piperidine]

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a 0° C. solution of [4-(spiro[indene-1,4′-piperidine]-1′-ylmethyl)phenyl]methanol (1.5 g, 4.91 mmol) in DCM (50 mL) is added phosphorus tribromide (0.667 mL, 6.8 mmol). The reaction mixture is stirred for 15 minutes at 0° C. The reaction mixture is diluted with water (100 mL) at 0° C. and extracted with DCM (2×200 mL). The combined extracts are washed with brine, dried over sodium sulfate, filtered, and concentrated to give the title compound as an off white solid (1.1 g, 61%). ESI/MS m/z 369 (M+H)+.

Workup

  1. extractionextracted with DCM (2×200 mL)
  2. washThe combined extracts are washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1bf8b3be4e25441eb364d00e4ca33792
Source dataset
uspto-grants-2013_02
Patent number
US08383642B2

Reaction notes

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