Water → 5-(Triphenylmethyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine

HRID 649514Notes

Reaction equation

HRID 649514 reaction equation
[S:1]1[C:9]2[CH2:8][CH2:7][NH:6][CH2:5][C:4]=2[CH:3]=[CH:2]1.C(N(CC)CC)C.[C:17]1([C:23](Cl)([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O>ClCCl>[C:17]1([C:23]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[N:6]2[CH2:7][CH2:8][C:9]3[S:1][CH:2]=[CH:3][C:4]=3[CH2:5]2)[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6456Trityl chlorideHCID 8471TriethylamineHCID 30850764,5,6,7-Tetrahydrothieno(3,2-c)pyridine

Product 1

HCID 137484615-(Triphenylmethyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridineYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 100 g (0.718 mole) of 4,5,6,7-tetrahydro thieno [3,2-c]pyridine in 200 ml of dichloromethane, are added 80 ml (0.789 mole) of triethylamine, then 200.2 g (0.718 mole) of triphenylmethylchloride is added, drop by drop, at ambient temperature. The reaction medium is left overnight at ambient temperature. The reaction medium is poured into 2000 ml of water. The organic phase is decanted, dried over sodium sulfate and evaporated to dryness. The residue is purified by filtration on a silica bed (elution with dichloromethane). The product is white crystals, M.P.=95° C. (pasty); yield: 96%; NMR 1H (in ppm) (CDC13): 7.57-6.90 (m, 15H); 6.80 (c, J =6.5 Hz, 1H); 6.43 (d, J=6.5 Hz, 1H); 3.35 (s, 14), 3.00-2.33 (m, 4H).

Workup

  1. customat ambient temperature
  2. customThe organic phase is decanted
  3. dry with materialdried over sodium sulfate
  4. customevaporated to dryness
  5. filtrationThe residue is purified by filtration on a silica bed (elution with dichloromethane)

Sources & evidence

ORD record
ord-6ababfb908b444dc96346b73166ec988
Source dataset
uspto-grants-1988_04
Patent number
US04740510

Reaction notes

Loading…