Formaldehyde → Benzyl 4-(7-methoxy-2,3,4,5-tetrahydrobenzo[f][1,4]thiazepine-4-carbonyl)piperazine-1-carboxylate

HRID 1917073Notes

Reaction equation

HRID 1917073 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9][CH2:10][CH2:11][NH:12][C:13]([N:15]2[CH2:20][CH2:19][N:18]([C:21]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[O:22])[CH2:17][CH2:16]2)=[O:14])=[CH:5][CH:4]=1.C=O.[C:33]1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[S:9][CH2:10][CH2:11][N:12]([C:13]([N:15]3[CH2:20][CH2:19][N:18]([C:21]([O:23][CH2:24][C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)=[O:22])[CH2:17][CH2:16]3)=[O:14])[CH2:33][C:7]=2[CH:8]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 6101p-Toluenesulfonic acidHCID 68626717Benzyl 4-(2-(4-methoxyphenylthio)ethylcarbamoyl)piperazine-1-carboxylate

Product 1

HCID 68639517Benzyl 4-(7-methoxy-2,3,4,5-tetrahydrobenzo[f][1,4]thiazepine-4-carbonyl)piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
72.5 °C

Procedure

A mixture of compound 18 (30 mg), paraformaldehyde (100 mg), p-toluenesulfonic acid (30 mg) in benzene (5 mL) was stirred at 70-75° C. for 2 days. The reaction mixture was filtered, washed with sat. NaHCO3 and concentrated to give crude product 19, which was purified by chromatography on SiO2 (CH2Cl2/EtOAc 10:1). Yield: 21 mg, 69%.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washwashed with sat. NaHCO3
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-cf7ef04c2d2c430f8b23f2c0fcb441b2
Source dataset
uspto-grants-2013_12
Patent number
US08618282B2

Reaction notes

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