Ammonia → HCID 22750688, compound

HRID 1606127Notes

Reaction equation

HRID 1606127 reaction equation
N.[Na].[CH3:3][C:4]1[C:14]2[CH2:13][CH2:12][C:11]3[CH:15]=[CH:16][CH:17]=[CH:18][C:10]=3[C:9](=[O:19])[C:8]=2[CH:7]=[CH:6][CH:5]=1.Cl[CH2:21][CH2:22][CH2:23][NH2:24]>O.C1(C)C=CC=CC=1>[CH3:3][C:4]1[C:14]2[CH2:13][CH2:12][C:11]3[CH:15]=[CH:16][CH:17]=[CH:18][C:10]=3[C:9]([CH2:21][CH2:22][CH2:23][N:24]=[CH:3][C:4]3[CH:14]=[CH:8][CH:7]=[CH:6][CH:5]=3)([OH:19])[C:8]=2[CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 222Ammonia3×HCID 846293-ChloropropylamineHCID 5360545Sodium2×HCID 20067572HCID 20067572, compound

Product 1

HCID 22750688HCID 22750688, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Conditions

Temperature
80 °C

Procedure

To a 250 ml. 3-neck vessel, equipped with a stirrer, a dropping funnel and an ammonia coolant, are added 75 ml. of liquid ammonia, and it is treated by adding a sodium chip to obtain a stable blue color. A solution containing 22.2 g. of 1-methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-one in 50 ml. of dry toluene is added dropwise with stirring. Thereafter, 4.6 g. of sodium are added piece by piece over a 30-minute period. The mixture is stirred for an additional 30 minutes and a solution containing 11.4 g. of freshly distilled 1-chloro-3-aminopropane in 40 ml. of dry toluene is added. The ammonia coolant is replaced by a water-cooler and the mixture is stirred overnight. The following morning, the mixture is cautiously decomposed with 50 ml. of water, whereby the 1-methyl-10,11-dihydro-5-(3-aminopropyl)-5-hydroxy-5H-dibenzo[a,d]cycloheptene partially crystallizes. Its melting point, after recrystallization from benzene/petroleum ether, is 155°-156°C. The crystals are removed by filtration and together with the separated toluene layer are treated with 13 g. of freshly distilled benzaldehyde. The mixture is heated at 80°C. under reduced pressure, so that the toluene and the residual water distil over. After recrystallization of the residue from ethanol, there is obtained 1-methyl-10,11-dihydro-5-(3-benzylideneaminopropyl)-5-hydroxy-5H-dibenzo [a,d]cycloheptene as colorless crystals having a melting point of 130°-131°C.

Workup

  1. custom3-neck vessel, equipped with a stirrer, a dropping funnel
  2. customto obtain a stable blue color
  3. additionA solution containing 22.2 g
  4. stirringThe mixture is stirred for an additional 30 minutes
  5. additiona solution containing 11.4 g
  6. stirringthe mixture is stirred overnight
  7. customof water, whereby the 1-methyl-10,11-dihydro-5-(3-aminopropyl)-5-hydroxy-5H-dibenzo[a,d]cycloheptene partially crystallizes
  8. customafter recrystallization from benzene/petroleum ether
  9. customis 155°-156°C
  10. customThe crystals are removed by filtration and together with the separated toluene layer
  11. additionare treated with 13 g
  12. customthe residual water distil over
  13. customAfter recrystallization of the residue from ethanol

Sources & evidence

ORD record
ord-567b492e0e284345af19119d91208309
Source dataset
uspto-grants-1976_04
Patent number
US03952017

Reaction notes

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