Hydrochloric Acid → HCID 9902422, compound

HRID 482734Notes

Reaction equation

HRID 482734 reaction equation
[NH2:1][CH:2]1[CH2:8][CH2:7][C:6]2[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=2[NH:4][C:3]1=[O:13].[CH2:14]([CH2:21][C:22](=O)[C:23]([OH:25])=[O:24])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C([BH3-])#N.[Na+].Cl>CO>[C:23]([CH:22]([NH:1][CH:2]1[CH2:8][CH2:7][C:6]2[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=2[NH:4][C:3]1=[O:13])[CH2:21][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([OH:25])=[O:24]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 697322-Oxo-4-phenylbutyric acidHCID 44344333-Amino-2,3,4,5-tetrahydro-1H-benzazepin-2-oneHCID 5003444Sodium cyanoborohydride

Product 1

HCID 9902422HCID 9902422, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3-amino-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-one (8.0 g) and benzylpyruvic acid (18.0 g) in methanol (450 ml) was stirred at room temperature under nitrogen for 30 minutes. Sodium cyanoborohydride (4.5 g) was added, and the resulting solution stirred at room temperature for 48 hours. Concentrated hydrochloric acid (7 ml) was added dropwise during 10 minutes and stirring was maintained for an additional 1 hour. The reaction mixture was evaporated to dryness, dichloromethane (150 ml) was added, and the mixture stirred for 30 minutes. The solid was filtered off, stirred with water (100 ml) for 15 minutes, then filtered, washed with water (50 ml), and dried to give 3-(1-carboxy-3-phenylpropylamino)-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-one, m.p. 173°-175° as a mixture of isomers.

Workup

  1. stirringstirring
  2. temperaturewas maintained for an additional 1 hour
  3. customThe reaction mixture was evaporated to dryness, dichloromethane (150 ml)
  4. additionwas added
  5. stirringthe mixture stirred for 30 minutes
  6. filtrationThe solid was filtered off
  7. stirringstirred with water (100 ml) for 15 minutes
  8. filtrationfiltered
  9. washwashed with water (50 ml)
  10. customdried

Sources & evidence

ORD record
ord-a84cf52f0bd5430ebc62c0452f598f21
Source dataset
uspto-grants-1986_03
Patent number
US04575503

Reaction notes

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