Tetrahydrofuran → HCID 21192595, compound

HRID 1068042Notes

Reaction equation

HRID 1068042 reaction equation
[NH2:1][C:2]1[CH:14]=[CH:13][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][O:10][CH2:9][CH2:8]2)=[CH:4][CH:3]=1.O1CCCC1.[S:20]1[CH2:25][CH2:24][C:23](=O)[CH2:22][CH2:21]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(O)(=O)C>[N:7]1([CH2:6][C:5]2[CH:13]=[CH:14][C:2]([NH:1][CH:23]3[CH2:24][CH2:25][S:20][CH2:21][CH2:22]3)=[CH:3][CH:4]=2)[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 66173Tetrahydrothiopyran-4-oneHCID 7768514-(Morpholinomethyl)anilineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 21192595HCID 21192595, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A flask containing 4-(4-aminobenzyl)morpholine from Preparation No. 22 (0.48 g) is treated with tetrahydrofuran (10 mL) and terahydrothiopyran-4-one (0.35 gm) under an argon atmosphere. The solution is treated with acetic acid (0.20 mL) followed by sodium triacetoxyborohydride (0.80 g). After stirring overnight, the mixture is concentrated under reduced pressure. The residue is partitioned between dichloromethane and dilute aqueous sodium hydroxide. The aqueous is back-extracted with dichloromethane. The combined organic layers are washed with brine, dried over sodium sulfate, and concentrated under reduced pressure. The residue is purified by flash column chromatography on silica eluting with 2% to 6% methanol in dichloromethane and then by recrystallization from cyclohexane to afford 0.53 g of N-[4-(4-morpholinylmethyl)phenyl]tetrahydro-2H-thiopyran-4-amine as a tan solid.

Workup

  1. customfrom Preparation No
  2. concentrationthe mixture is concentrated under reduced pressure
  3. customThe residue is partitioned between dichloromethane and dilute aqueous sodium hydroxide
  4. extractionThe aqueous is back-extracted with dichloromethane
  5. washThe combined organic layers are washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue is purified by flash column chromatography on silica eluting with 2% to 6% methanol in dichloromethane
  9. customby recrystallization from cyclohexane

Sources & evidence

ORD record
ord-2e38ae8007f34d1dbc43412c95c10ec7
Source dataset
uspto-grants-2001_06
Patent number
US06248739B1

Reaction notes

Loading…