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Ammonia → HCID 13056027, compound

HRID 2198757
Notes
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Reaction equation

HRID 2198757 reaction equation
O=[C:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][CH2:10][N:11]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[NH:13][C:12]2=[O:20])[CH2:4][CH2:3]1.[CH3:21][N:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[CH:23]1.P(=O)(O)(O)O.N>C(O)(=O)C>[CH3:21][N:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:24]([CH:2]2[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][CH2:10][N:11]3[C:15]4[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=4[NH:13][C:12]3=[O:20])[CH2:4][CH2:3]2)=[CH:23]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 222AmmoniaHCID 1004Phosphoric AcidHCID 117811-MethylindoleHCID 13056043N-[3-(4-oxo-piperidino)-propyl]-benzimidazolone

Product 1

HCID 13056027HCID 13056027, compound

Reagents, catalysts & solvents 1

HCID 176Acetic Acid
Solvent

Procedure

A mixture consisting of 2.7 gm of N-[3-(4-oxo-piperidino)-propyl]-benzimidazolone, 1.3 gm of 1-methylindole, 40 ml of acetic acid and 10 ml of 2 N phosphoric acid was allowed to stand at 20° C. for 6 days. Thereafter, the reaction mixture was poured into a mixture of ice and ammonia, the aqueous mixture was extracted with ethyl acetate, and the extract solution was dried and evaporated in vacuo to dryness. The residue was purified by chromatography on silica, using methylene chloride/methanol/ammonia=90/9/1 as the eluant. The main fraction was hydrogenated without characterization as described in Example 1, and the end product was crystallized from ethanol, yielding 2.4 gm (62% of theory) of the compound of the formula ##STR14## having a melting point of 180° C.

Workup

  1. extractionthe aqueous mixture was extracted with ethyl acetate
  2. customthe extract solution was dried
  3. customevaporated in vacuo to dryness
  4. customThe residue was purified by chromatography on silica
  5. customthe end product was crystallized from ethanol
  6. customyielding 2.4 gm (62% of theory) of the compound of the formula

Sources & evidence

ORD record
ord-877f600815624a71bee134eec044f646
Source dataset
uspto-grants-1982_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04359468

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes