1,2-Diphenylethylamine → HCID 86737709, compound

HRID 444507

Reaction equation

HRID 444507 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1([C:13]([OH:15])=[O:14])[CH2:12][CH2:11][CH:10]=[N:9]1.[C:16]1([CH:22]([NH2:30])[CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>>[C:16]1([CH:22]([NH2:30])[CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1([C:13]([OH:15])=[O:14])[CH2:12][CH2:11][CH:10]=[N:9]1

Participants

3

Reactant 2

HCID 264821,2-DiphenylethylamineHCID 70573103(+/-)-2-(2-Hydroxyphenyl)-5-pyrrolinecarboxylic acid

Product 1

HCID 86737709HCID 86737709, compound

Procedure

35.8 g of (±)-2-(2-hydroxyphenyl)-5-pyrrolinecarboxylic acid is reacted with 34.5 g of (-)-1,2-diphenylethylamine to give the diastereoisomer salt. The salt is fractionally recrystallized from ethanol to give (-)-2-(2-hydroxyphenyl)-5-pyrrolinecarboxylic acid (-)-1,2-diphenylethylamine salt, yield 20.0 g (57%), mp. 193°-194° C., [α]D26 -90.0° (c=1.0, methanol). The residual salt in the filtrate is fractionally recrystallized from chloroform to give (+)-2-(2-hydroxyphenyl)-5-pyrrolinecarboxylic acid (-)-1,2-diphenylethylamine salt, yield 18.0 g (51%), mp. 138°-140° C., [α]D26 -20.3° (c=1.2, methanol).

Workup

  1. customto give the diastereoisomer salt
  2. customThe salt is fractionally recrystallized from ethanol

Sources & evidence

ORD record
ord-4dcc99396c6d4586a5839fa6870f45fc
Source dataset
uspto-grants-1981_04
Patent number
US04264620

Linked notes

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