Water → HCID 54086598, compound

HRID 2108041Notes

Reaction equation

HRID 2108041 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[NH2:8][C:9]1[C:14]([Cl:15])=[CH:13][C:12]([CH:16]([CH2:18][NH:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][O:26][CH2:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=2)[OH:17])=[CH:11][C:10]=1[Cl:35].O.[CH3:37][CH2:38][O:39]CC>N1C=CC=CC=1>[C:1]([O:17][CH:16]([CH2:18][N:19]([C:38](=[O:39])[CH3:37])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][O:26][CH2:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=1)[C:12]1[CH:13]=[C:14]([Cl:15])[C:9]([NH2:8])=[C:10]([Cl:35])[CH:11]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 7918Acetic Anhydride2×HCID 9954184HCID 9954184, compound

Product 1

HCID 54086598HCID 54086598, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent3×

Procedure

Acetic anhydride (132 mg) in pyridine (2 ml) was added dropwise to a solution of 4-amino-3,5-dichloro-α-[[[6-[2-(2-pyridinyl)ethoxy]hexyl]amino]methyl]benzenemethanol (250 mg) in pyridine (2 ml). The solution was stirred under nitrogen at room temperature overnight and more acetic anhydride (66 mg) in pyridine was added. After stirring for a further 12 h, the solution was evaporated in vacuo to give an oil which was partioned between water (5 ml) and ether (5 ml). The aqueous layer was re-extracted with ether (5 ml) and the combined organic layers were dried and concentrated to give the title compound as a clear oil (190 mg), t.l.c. (System A 80:20:1) Rf 0.5.

Workup

  1. stirringAfter stirring for a further 12 h
  2. customthe solution was evaporated in vacuo
  3. customto give an oil which
  4. extractionThe aqueous layer was re-extracted with ether (5 ml)
  5. customthe combined organic layers were dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ce428a8a6cae494a819117156104ca55
Source dataset
uspto-grants-1990_06
Patent number
US04937251

Reaction notes

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