Ammonia → HCID 18797028, compound

HRID 1003706Notes

Reaction equation

HRID 1003706 reaction equation
C[O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][N:9]([CH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:18](=[O:31])[C:19]3[CH:24]=[CH:23][C:22]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[CH:21][CH:20]=3)[CH2:10]2)=[CH:5][CH:4]=1.N>ClCCl>[OH:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][N:9]([CH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:18](=[O:31])[C:19]3[CH:20]=[CH:21][C:22]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[CH:23][CH:24]=3)[CH2:10]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 187970217-Methoxy-N-(4-(4-phenylbenzoylamino)butyl)-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 18797028HCID 18797028, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of borontribromide i n dichloromethane (72 ml, 1M solution, 72 mmol) was added dropwise with stirring to an ice-cooled solution of 7-methoxy-N-(4-(4-phenylbenzoylamino)butyl)-1,2,3,4-tetrahydroisoquinoline (5.00 g, 12.1 mmol) in dichloromethane (150 ml). After stirring at room temperature for 16 h the reaction mixture was poured onto a mixture of crushed-ice (200 g) and 0.880 aqueous ammonia (400 ml). The resulting mixture was extracted with dichloromethane (3×200 ml). The combined organics were washed with brine (200 ml) then dried (Na2SO4) and the solvent evaporated in vacuo to give the title compound as a pale yellow solid (3.60 g, 75%).

Workup

  1. additionwas added dropwise
  2. additionwas poured onto a mixture
  3. extractionThe resulting mixture was extracted with dichloromethane (3×200 ml)
  4. washThe combined organics were washed with brine (200 ml)
  5. dry with materialthen dried (Na2SO4)
  6. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-2ff9553796774acfbc3181f998897a98
Source dataset
uspto-grants-2000_04
Patent number
US06046210

Reaction notes

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