Sulfuric Acid → HCID 59655727, compound

HRID 2054401Notes

Reaction equation

HRID 2054401 reaction equation
[CH:1]([N:14]1[CH2:17][C:16]([N:20]([CH3:22])[CH3:21])([C:18]#[N:19])[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:23]S(O)(=O)=O>C(Cl)Cl>[CH:1]([N:14]1[CH2:17][C:16]([N:20]([CH3:22])[CH3:21])([C:18]([NH2:19])=[O:23])[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 59655723HCID 59655723, compound

Product 1

HCID 59655727HCID 59655727, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A vigorously stirred solution of 1-benzhydryl-3-dimethylaminoazetidine-3-carbonitrile (I-3A-3a; 1.55 g, 5.32 mmol) in methylene chloride (30 ml) cooled in an ice bath was treated with H2SO4 (3.0 ml, 54 mmol), dropwise. After warming to room temperature and stirring overnight, the reaction was cooled in an ice bath and then carefully quenched with concentrated aqueous NH4OH to pH 11. The mixture was extracted with methylene chloride. The combined organic layers were dried (Na2SO4) and then concentrated. The crude product (4:1 product to starting material) was then purified on a Biotage™ Flash 40M column using 3% methanol in methylene chloride as eluant. The residue (1.04 g) was then triturated from ether to afford I-3A-3b (0.75 g, 45%): +ESI MS (M+1) 310.3; 1H NMR (400 MHz, CD3OD) δ 7.40 (d, J=7.5 Hz, 4H), 7.24 (t, J=7.5 Hz, 4H), 7.17 (t, J=7.3 Hz, 2H), 4.42 (s, 1H), 3.41 (d, J=8.7 Hz, 2H), 3.12 (d, J=8.7 Hz, 2H), 2.26 (s, 6H).

Workup

  1. temperaturethe reaction was cooled in an ice bath
  2. customcarefully quenched with concentrated aqueous NH4OH to pH 11
  3. extractionThe mixture was extracted with methylene chloride
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. concentrationconcentrated
  6. customThe crude product (4:1 product to starting material) was then purified on a Biotage™ Flash 40M column
  7. customThe residue (1.04 g) was then triturated from ether
  8. customto afford I-3A-3b (0.75 g, 45%)

Sources & evidence

ORD record
ord-96c3cbcb607e469f859f1729b8bad145
Source dataset
uspto-grants-2008_02
Patent number
US07329658B2

Reaction notes

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