Benzyl chloroformate → HCID 86735958, compound

HRID 427051Notes

Reaction equation

HRID 427051 reaction equation
Br.[OH:2][C:3]1[C:19]([OH:20])=[CH:18][C:6]2[CH:7]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH2:8][NH:9][CH2:10][CH2:11][C:5]=2[CH:4]=1.[OH-].[Na+].[C:23](Cl)([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24]>CN(C)C=O>[OH:2][C:3]1[C:19]([OH:20])=[CH:18][C:6]2[CH:7]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH2:8][N:9]([C:23]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[O:24])[CH2:10][CH2:11][C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 14798Sodium HydroxideHCID 12928470SKF-38393 (hydrobromide)

Product 1

HCID 86735958HCID 86735958, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 7.10 g. (18.6 mole) of 7,8-dihydroxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrobromide in 120 ml. of aqueous dimethyl-formamide at 0° under an argon atmosphere is basified to pH 10.0 with 10% sodium hydroxide solution. To this cold mixture is added 13.0 g. (76 mole) of carbobenzyloxy chloride in small portions over 15 minutes with concomitant addition of 10% alkali so as to maintain a pH of 10 to 10.5. The reaction is allowed to warm to room temperature after stirring at 0° for one and one-half hours. The mixture is diluted with saturated salt and extracted with three portions of ethyl acetate. The combined organic extract is backwashed twice with saturated salt. The dried extract is concentrated in vacuo and heated at 75°/0.1 mm Hg to remove any benzyl alcohol to yield 7,8-dihydroxy-N-carbobenzyloxy-1-phenyl-2,3,4,5-tetrahydro-1-H-3-benzazepine.

Workup

  1. customat 0°
  2. additionTo this cold mixture is added 13.0 g
  3. temperatureto maintain a pH of 10 to 10.5
  4. additionThe mixture is diluted with saturated salt
  5. extractionextracted with three portions of ethyl acetate
  6. extractionThe combined organic extract
  7. extractionThe dried extract
  8. concentrationis concentrated in vacuo
  9. temperatureheated at 75°/0.1 mm Hg
  10. customto remove any benzyl alcohol

Sources & evidence

ORD record
ord-b7ad072b1514440fa1732efd89c8d780
Source dataset
uspto-grants-1979_10
Patent number
US04172890

Reaction notes

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