Hydrogen Bromide → HCID 21435478, compound

HRID 1580860Notes

Reaction equation

HRID 1580860 reaction equation
[CH2:1]([N:8]([CH2:37][CH2:38][C:39]1[CH:44]=[CH:43][C:42]([O:45]C)=[C:41]([C:47]([O:49]C)=[O:48])[CH:40]=1)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][N:15]([CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24]C)=[C:20]([C:26]([O:28]C)=[O:27])[CH:19]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BrH:51]>>[BrH:51].[BrH:51].[CH2:1]([N:8]([CH2:37][CH2:38][C:39]1[CH:44]=[CH:43][C:42]([OH:45])=[C:41]([C:47]([OH:49])=[O:48])[CH:40]=1)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][N:15]([CH2:30][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[C:20]([C:26]([OH:28])=[O:27])[CH:19]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 21435554HCID 21435554, compound

Product 1

HCID 21435478HCID 21435478, compound

Procedure

A mixture of 1.56 g. (0.0023 m.) of N,N'-dibenzyl-N,N'-bis[2-(3-carbomethoxy-4-methoxyphenyl)-ethyl]-hexamethylenediamine and 40 ml. of 48% aqueous hydrobromic acid is refluxed for four hours. The cooled reaction mixture is filtered to give N,N'-dibenzyl-N,N'-bis[2-(3-carboxy-4-hydroxyphenyl)-ethyl]-hexamethylenediamine dihydrobromide. The latter is hydrogenated with palladium-on-carbon as described in Example 1 to yield N,N'-bis[2-(3-carboxy-4-hydroxyphenyl)-ethyl]-hexamethylenediamine dihydrobromide. The free base obtained from this dihydrobromide (0.8 g., 0.0018 m.) is added to an ice cold solution of 40 ml. of 1M borane in tetrahydrofuran (0.04 m.) while stirring under nitrogen. The temperature is maintained at 0°C. for 20 hours, the solution is then refluxed for one hour and concentrated in vacuo. Several portions of methanol are added, the solution is concentrated and the residue is dissolved in ethanol and filtered. Sulfuric acid is added to pH 2.0 to give N,N'-bis[2-(4-hydroxy-3-hydroxymethylphenyl)-ethyl]-hexamethylenediamine sulfate.

Workup

  1. additionA mixture of 1.56 g
  2. customThe cooled reaction mixture
  3. filtrationis filtered

Sources & evidence

ORD record
ord-f34439a57b2c4e49ac9ff1c0458fe93d
Source dataset
uspto-grants-1976_01
Patent number
US03933913

Reaction notes

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