HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Water → 5-(4-isopropyl-2-morpholinylmethyl)-10,11-dihydro-5H-dibenz[b,f]azepine

HRID 328581
Notes
Print preview

Reaction equation

HRID 328581 reaction equation
[NH2-].[Na+].[CH:3]1[C:13]2[CH2:12][CH2:11][C:10]3[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=3[NH:8][C:7]=2[CH:6]=[CH:5][CH:4]=1.[CH:18]([N:21]1[CH2:26][CH2:25][O:24][CH:23]([CH2:27]Cl)[CH2:22]1)([CH3:20])[CH3:19].O>C1C=CC=CC=1>[CH:18]([N:21]1[CH2:26][CH2:25][O:24][CH:23]([CH2:27][N:8]2[C:9]3[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=3[CH2:11][CH2:12][C:13]3[CH:3]=[CH:4][CH:5]=[CH:6][C:7]2=3)[CH2:22]1)([CH3:20])[CH3:19]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 10308IminodibenylHCID 24533Sodium amideHCID 128324802-(Chloromethyl)-4-(propan-2-yl)morpholine

Product 1

HCID 214427915-(4-isopropyl-2-morpholinylmethyl)-10,11-dihydro-5H-dibenz[b,f]azepine

Reagents, catalysts & solvents 1

HCID 241
Benzene
Solvent
3×

Procedure

To a suspension of sodium amide (0.5 g) in benzene was added a solution of 10,11-dihydro-5H-dibenz[b,f]azepine (1.0 g) in benzene at room temperature, and the resulting mixture was stirred under reflux for 1 hour. After cooling, a solution of 4-isopropyl-2-chloromethylmorpholine (1.0 g) in benzene was added to the reaction mixture at room temperature, and the resulting mixture was stirred at room temperature for 1 hour and refluxed for 20 hours with stirring. The reaction mixture was cooled and admixed with water. The benzene layer was separated, washed with water, dried over anhydrous magnesium sulfate and evaporated to afford 5-(4-isopropyl-2-morpholinylmethyl)-10,11-dihydro-5H-dibenz[b,f]azepine as an oily substance. M.P. 203.5° -- 204.5° C (oxalate).

Workup

  1. temperatureunder reflux for 1 hour
  2. temperatureAfter cooling
  3. stirringthe resulting mixture was stirred at room temperature for 1 hour
  4. temperaturerefluxed for 20 hours
  5. stirringwith stirring
  6. temperatureThe reaction mixture was cooled
  7. customThe benzene layer was separated
  8. washwashed with water
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customevaporated

Sources & evidence

ORD record
ord-8cadcf62a44d4ee4ba6e649edb8b39cf
Source dataset
uspto-grants-1977_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04017621

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes