Trimethyl orthoformate → HCID 22254656, compound

HRID 1611659Notes

Reaction equation

HRID 1611659 reaction equation
[NH2:1][C:2]1[CH:24]=[CH:23][CH:22]=[CH:21][C:3]=1[NH:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[CH2:7][CH2:6]1.[CH:25](OC)(OC)OC>O>[C:15]1([CH2:14][O:13][C:11]([N:8]2[CH2:7][CH2:6][CH:5]([N:4]3[C:3]4[CH:21]=[CH:22][CH:23]=[CH:24][C:2]=4[N:1]=[CH:25]3)[CH2:10][CH2:9]2)=[O:12])[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 9005Trimethyl orthoformateHCID 22254643HCID 22254643, compound

Product 1

HCID 22254656HCID 22254656, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2-amino-1-N-[1-(phenylmethyloxycarbonyl)-piperidin-4-yl]aniline (Method C) (500 mg, 1.4 mmol), trimethyl orthoformate (1 ml, 9.7 mmol) and para-toluenesuphonic acid monohydrate (30 mg, 0.16 mmol) were stirred at 100° C. After 2 h the mixture was cooled and water (10 ml) was added. The solution was partitioned with EtOAc (3×20 ml) then the organics were combined, washed with water (10 ml), dried (MgSO4) and concentrated to give the title compound as an oil that did not need further purification (410 mg, 1.2 mmol); NMR: 2.0 (m, 4H), 3.0 (m, 2H), 4.2 (d, 2H), 4.6 (m, 1H), 5.1 (s, 2H), 7.2 (m, 2H), 7.4 (m, 5H), 7.65 (d, 2H) and 8.3 (s, 1H); MS: 336.

Workup

  1. temperatureAfter 2 h the mixture was cooled
  2. customThe solution was partitioned with EtOAc (3×20 ml)
  3. washwashed with water (10 ml)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b6c711b069934b9c9aff5e3e6a115472
Source dataset
uspto-grants-2006_01
Patent number
US06989393B2

Reaction notes

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