4-Nitrophenyl chloroformate → 4-Nitrophenyl [3-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)phenyl]carbamate hydrochloride

HRID 1295431Notes

Reaction equation

HRID 1295431 reaction equation
[Cl:1]C1C=C2C(=C(Cl)C=1)CN(C)CC2C1C=C(N)C=CC=1.[Cl:21][C:22]1[CH:23]=[C:24]2[C:29](=[C:30]([Cl:32])[CH:31]=1)[CH2:28][N:27]([CH3:33])[CH2:26][CH:25]2[C:34]1[CH:35]=[C:36]([NH:40][C:41](=[O:52])[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO)[CH:37]=[CH:38][CH:39]=1.ClC1C=C2C(=C(Cl)C=1)CN(C)CC2C1C=CC([C@@](O)([C@@H](O)[C@H](O)[C@H](O)CO)C(N)=O)=CC=1.ClC([O:88][C:89]1[CH:94]=[CH:93][C:92]([N+:95]([O-:97])=[O:96])=[CH:91][CH:90]=1)=O>ClCCl>[ClH:1].[Cl:21][C:22]1[CH:23]=[C:24]2[C:29](=[C:30]([Cl:32])[CH:31]=1)[CH2:28][N:27]([CH3:33])[CH2:26][CH:25]2[C:34]1[CH:35]=[C:36]([NH:40][C:41](=[O:52])[O:88][C:89]2[CH:94]=[CH:93][C:92]([N+:95]([O-:97])=[O:96])=[CH:91][CH:90]=2)[CH:37]=[CH:38][CH:39]=1

Participants

6

Reactant 4

HCID 821294-Nitrophenyl chloroformate2×HCID 98361943-(6,8-Dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)anilineHCID 11213884N-[3-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)phenyl]-(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanamideHCID 69511913[4-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)phenyl]-(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanamide

Product 1

HCID 223868924-Nitrophenyl [3-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)phenyl]carbamate hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

350 mg (1.1 mmol) of 3-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)phenylamine (Example compound 2, intermediate 1) were dissolved in 17.5 ml of dichloromethane and admixed with stirring with 230 mg (1.1 mmol) of 4-nitrophenyl chloroformate. After 4.5 hours, a further 0.1 equivalent (23 mg) of 4-nitrophenyl chloroformate was added and the solution was stirred overnight. For workup, the resulting precipitate was filtered off and washed with dichloromethane. The crude product obtained in this way could be reacted further without further purification.

Workup

  1. filtrationFor workup, the resulting precipitate was filtered off
  2. washwashed with dichloromethane

Sources & evidence

ORD record
ord-3fb6f50621124956a0f1f53efef6829b
Source dataset
uspto-grants-2007_07
Patent number
US07241775B2

Reaction notes

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