Formaldehyde → 4-[2-(1-Methyl-piperidin-4-yl)-thiazol-4-yl]-benzoic acid

HRID 606605Notes

Reaction equation

HRID 606605 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]2[S:8][CH:9]=[C:10]([C:12]3[CH:20]=[CH:19][C:15]([C:16]([OH:18])=[O:17])=[CH:14][CH:13]=3)[N:11]=2)[CH2:3][CH2:2]1.[CH2:21]=O>C(O)(=O)C.CO.O1CCCC1>[CH3:21][N:1]1[CH2:6][CH2:5][CH:4]([C:7]2[S:8][CH:9]=[C:10]([C:12]3[CH:20]=[CH:19][C:15]([C:16]([OH:18])=[O:17])=[CH:14][CH:13]=3)[N:11]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 2

HCID 712FormaldehydeHCID 582568334-[2-(Piperidin-4-yl)-1,3-thiazol-4-yl]benzoic acid

Product 1

HCID 116018794-[2-(1-Methyl-piperidin-4-yl)-thiazol-4-yl]-benzoic acid

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(2-Piperidin-4-yl-thiazol-4-yl)-benzoic acid (1 mmol) in acetic acid (0.5 mL), methanol (3 mL) and tetrahydrofurane (4.5 mL) was added formaldehyde (aq. 37%, 300 mL) and polystyrene bound cyanoborohydride (2.36 mmol/g, 900 mg). The slurry was then agitated for 16 hours at room temperature. The slurry was then filtered and the resin washed with methanol (2 mL). The solution was concentrated to dryness in vacuo. m/z=303.1 in MS ES+, which was characterized by hplc and MS and used in the next step without any further purification.

Workup

  1. filtrationThe slurry was then filtered
  2. washthe resin washed with methanol (2 mL)
  3. concentrationThe solution was concentrated to dryness in vacuo
  4. customused in the next step without any further purification

Sources & evidence

ORD record
ord-b6590f904241455dbde0db570ae60d50
Source dataset
uspto-grants-2011_03
Patent number
US07915300B2

Reaction notes

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