Chloroform → 3-(4-Isopropylphenyl)-4,6,7-trimethylspiro[benzofuran-2(3H),4'-piperidine]-5-ol Hydrochloride

HRID 1743201Notes

Reaction equation

HRID 1743201 reaction equation
C([N:8]1[CH2:13][CH2:12][C:11]2([CH:17]([C:18]3[CH:23]=[CH:22][C:21]([CH:24]([CH3:26])[CH3:25])=[CH:20][CH:19]=3)[C:16]3[C:27]([CH3:34])=[C:28]([OH:33])[C:29]([CH3:32])=[C:30]([CH3:31])[C:15]=3[O:14]2)[CH2:10][CH2:9]1)C1C=CC=CC=1.C(N(CC)CC)C.C(Cl)(Cl)[Cl:43]>>[ClH:43].[CH:24]([C:21]1[CH:20]=[CH:19][C:18]([CH:17]2[C:11]3([CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)[O:14][C:15]3[C:30]([CH3:31])=[C:29]([CH3:32])[C:28]([OH:33])=[C:27]([CH3:34])[C:16]2=3)=[CH:23][CH:22]=1)([CH3:26])[CH3:25]

Participants

4

Reactant 3

HCID 6212ChloroformHCID 8471TriethylamineHCID 222382651'-Benzyl-3-(4-isopropylphenyl)-4,6,7-trimethylspiro[benzofuran-2(3H), 4'-piperidine]-5-ol

Product 1

HCID 222382813-(4-Isopropylphenyl)-4,6,7-trimethylspiro[benzofuran-2(3H),4'-piperidine]-5-ol HydrochlorideYield 90.5%

Procedure

To a solution of 1′-benzyl-3-(4-isopropylphenyl)-4,6,7-trimethylspiro[benzofuran-2(3H),4′-piperidine]-5-ol (3.51 g, 7.70 mmol) and triethylamine (1.1 mL, 7.9 mmol) in chloroform (40 mL) α-chloroethyl chloroformate (2.30 g, 16.1 mmol) was added at 0° C. The mixture was refluxed for 1 hour and concentrated under reduced pressure. The residue was refluxed in methanol (20 mL) for 1 hour and concentrated under reduced pressure. The residue was crystallized from ethanol-ethyl acetate to obtain the title compound (2.80 g, yield 90%).

Workup

  1. temperatureThe mixture was refluxed for 1 hour
  2. concentrationconcentrated under reduced pressure
  3. temperatureThe residue was refluxed in methanol (20 mL) for 1 hour
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was crystallized from ethanol-ethyl acetate

Sources & evidence

ORD record
ord-59abd3dae8924a6da802c6ff7ac0f384
Source dataset
uspto-grants-2006_03
Patent number
US07008950B1

Reaction notes

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