1-(Carboethoxy)methyliminomethyl-3,4-dimethoxybenzene → N-[1-carboethoxy-5-(3,4-dimethoxyphenyl)-5-cyano-5-(isopropyl)pentyl]iminomethyl-3,4-dimethoxybenzene

HRID 979361Notes

Reaction equation

HRID 979361 reaction equation
[C:1]([CH2:6][N:7]=[CH:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([O:17][CH3:18])[CH:10]=1)([O:3][CH2:4][CH3:5])=[O:2].[Li]N(C(C)C)C(C)C.[CH3:27][O:28][C:29]1[CH:30]=[C:31]([C:37]([CH:44]([CH3:46])[CH3:45])([CH2:40][CH2:41][CH2:42]I)[C:38]#[N:39])[CH:32]=[CH:33][C:34]=1[O:35][CH3:36]>C1COCC1.CN(P(N(C)C)(N(C)C)=O)C>[C:1]([CH:6]([N:7]=[CH:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([O:17][CH3:18])[CH:10]=1)[CH2:42][CH2:41][CH2:40][C:37]([C:31]1[CH:32]=[CH:33][C:34]([O:35][CH3:36])=[C:29]([O:28][CH3:27])[CH:30]=1)([C:38]#[N:39])[CH:44]([CH3:46])[CH3:45])([O:3][CH2:4][CH3:5])=[O:2]

Participants

5

Reactant 3

HCID 112997121-(Carboethoxy)methyliminomethyl-3,4-dimethoxybenzeneHCID 140271622-(3,4-Dimethoxyphenyl)-2-isopropyl-2-(3-iodopropyl)acetonitrileHCID 178506924HCID 178506924, compound

Product 1

HCID 20202215N-[1-carboethoxy-5-(3,4-dimethoxyphenyl)-5-cyano-5-(isopropyl)pentyl]iminomethyl-3,4-dimethoxybenzene

Reagents, catalysts & solvents 1

HCID 86583969tetrahydrofuran HMPASolvent

Procedure

The resulting imine of formula 24 is then deprotonated using a suitable strong base, and allowed to react with a compound of formula 22 to produce a compound of formula 25 (step 2). For example, 1-(carboethoxy)methyliminomethyl-3,4-dimethoxybenzene (24) is suspended in a solution of LiNiPr2 in THF/HMPA at -78° C., then reacted with 2-(3,4-dimethoxyphenyl)-2-isopropyl-2-(3-iodopropyl)acetonitrile (22) to produce N-[1-carboethoxy-5-(3,4-dimethoxyphenyl)-5-cyano-5-(isopropyl)pentyl]iminomethyl-3,4-dimethoxybenzene (25).

Sources & evidence

ORD record
ord-65a993c6024f4160834289b85e2aec32
Source dataset
uspto-grants-1987_05
Patent number
US04667038

Reaction notes

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