Acetyl chloride → HCID 68754733, compound

HRID 1753981Notes

Reaction equation

HRID 1753981 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:3]=1[CH2:4][CH2:5][C:6]1([O:15]2)[CH2:11][CH2:10][N:9]([C:12](=S)[CH3:13])[CH2:8][CH2:7]1.Cl.ClC1C=CC=C2C=1CCC1([O:32]2)CCNCC1.CCN(CC)CC.C(Cl)(=O)C>C(Cl)Cl.O>[C:12]([N:9]1[CH2:10][CH2:11][C:6]2([CH2:5][CH2:4][C:3]3[C:16](=[CH:17][CH:18]=[CH:19][C:2]=3[Cl:1])[O:15]2)[CH2:7][CH2:8]1)(=[O:32])[CH3:13]

Participants

7

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 670881545-Chloro-3,4-dihydrospiro[1-benzopyran-2,4'-piperidine]--hydrogen chloride (1/1)HCID 86660455HCID 86660455, compound

Product 1

HCID 68754733HCID 68754733, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

5-Chloro-1′-ethanethioyl-3,4-dihydrospiro[chromene-2,4′-piperidine] To a suspension of 5-chloro-3,4-dihydrospiro[chromene-2,4′-piperidine] HCl salt (2 g, 7.3 mmol) and Et3N (3 mL, 21.5 mmol) in CH2Cl2 (25 mL) was added acetyl chloride (0.7 mL, 9.8 mmol). After stirring for 1 h, the mixture was diluted with water and extracted with CH2Cl2. The CH2Cl2 extract was washed with diluted brine, dried (MgSO4) and concentrated. The resulting residue was purified by Combi-Flash™ (40 g, 50-100% EtOAc in hexanes for 20 min, 40 mL/min, 18 mL/fraction) to give 1′-acetyl-5-chloro-3,4-dihydrospiro[chromene-2,4′-piperidine] as an oil, which solidified on standing.

Workup

  1. extractionextracted with CH2Cl2
  2. extractionThe CH2Cl2 extract
  3. washwas washed with diluted brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe resulting residue was purified by Combi-Flash™ (40 g, 50-100% EtOAc in hexanes for 20 min, 40 mL/min, 18 mL/fraction)

Sources & evidence

ORD record
ord-ee62878126dd4660b43a033839a1050c
Source dataset
uspto-grants-2015_10
Patent number
US09168248B2

Reaction notes

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