Hydrochloric Acid → HCID 21264424, compound

HRID 567106Notes

Reaction equation

HRID 567106 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:13]3[CH:14]=[CH:15][S:16][C:12]=3[CH2:11][CH2:10][NH:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:24][O:25][C:26]1[CH:33]=[CH:32][C:29]([CH2:30]Cl)=[CH:28][CH:27]=1.Cl>CN(C)C=O.C(OCC)C.O>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[C:13]3[CH:14]=[CH:15][S:16][C:12]=3[CH2:11][CH2:10][N:9]2[CH2:30][C:29]2[CH:32]=[CH:33][C:26]([O:25][CH3:24])=[CH:27][CH:28]=2)=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 699934-Methyloxybenzyl chlorideHCID 27392694-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine

Product 1

HCID 21264424HCID 21264424, compoundYield 67.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×HCID 6228DimethylformamideSolvent

Procedure

4-(4-Chlorophenyl)-4,5,6,7-tetrahydro-thieno[3,2-c]pyridine (0.10 g, 0.38 mmol) was dissolved in N,N-dimethylformamide (0.5 ml) and triethylamine (110 μl, 0.76 mmol) and 4-methoxybenzyl chloride (51 μl, 0.38 mmol) were added and the resulting mixture was shaken at 1000 rpm for 3 days. Water (2 ml) was added and the mixture was extracted with ethyl acetate (2×1 ml). The combined organic extracts were concentrated in vacuo. The residue was purified by preparative thin layer chromatography eluting with a mixture of ethyl acetate and heptane (1:4) to afford the free base. This was dissolved in diethyl ether and 1N HCl in diethyl ether was added drop wise to complete precipitation to afford 52 mg (34%) of the title compound.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (2×1 ml)
  2. concentrationThe combined organic extracts were concentrated in vacuo
  3. customThe residue was purified by preparative thin layer chromatography
  4. washeluting with a mixture of ethyl acetate and heptane (1:4)
  5. customto afford the free base
  6. customwise to complete precipitation

Sources & evidence

ORD record
ord-80b4e8ebef6e45d282e5e1e7b04fdbbc
Source dataset
uspto-grants-2001_01
Patent number
US06177443B1

Reaction notes

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