Hydrogen Bromide → (2-Amino-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-3-yl)phenylmethanone

HRID 566950Notes

Reaction equation

HRID 566950 reaction equation
[NH2:1][C:2]1[S:20][C:5]2[CH2:6][N:7](C(OCC3C=CC=CC=3)=O)[CH2:8][CH2:9][C:4]=2[C:3]=1[C:21](=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.Br.CCCCCC.[OH-].[Na+]>C(O)(=O)C.O>[NH2:1][C:2]1[S:20][C:5]2[CH2:6][NH:7][CH2:8][CH2:9][C:4]=2[C:3]=1[C:21](=[O:28])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

7

Reactant 4

HCID 260Hydrogen BromideHCID 8058HexaneHCID 14798Sodium HydroxideHCID 98218842-Amino-3-benzoyl-6-benzyloxycarbonyl4,5,6,7-tetrahydrothieno[2,3-c]pyridine

Product 1

HCID 15434454(2-Amino-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-3-yl)phenylmethanoneYield 92%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent

Procedure

To a cooled and stirred suspension of protected 2-amino-3-benzoyl-6-benzyloxycarbonyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine (0.01 mol) in acetic acid (2 mL), as prepared in Example 7, was added a solution of HBr (33%) in acetic acid (10 mL). After stirring at room temperature for 4 h (TLC control), n-hexane was added and the resulting suspension was evaporated under vacuum to give a solid which was dissolved in water (10 mL) and neutralized with NaOH (5% solution). The precipitated solid was chromatographed on a silica gel column eluting with an ethyl acetate and petroleum ether mixture to give 2-amino-3-benzoyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine. (m.p.160-162° C., 92% yield). 1H-NMR (CDCl3): 1.86 (m, 1 H); 1.95 (m, 2H); 2.79 (t, 2H); 3.79 (s, 2H).

Workup

  1. temperatureTo a cooled
  2. customas prepared in Example 7
  3. additionwas added
  4. customthe resulting suspension was evaporated under vacuum
  5. customto give a solid which
  6. customThe precipitated solid was chromatographed on a silica gel column
  7. washeluting with an ethyl acetate and petroleum ether mixture

Sources & evidence

ORD record
ord-e4cdce93ebc14690a05f5bee5536332b
Source dataset
uspto-grants-2001_01
Patent number
US06177444B1

Reaction notes

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