1-Pyrrolidinecarbonyl chloride → 1,2,3,4-Tetrahydroisoquinoline

HRID 1920769Notes

Reaction equation

HRID 1920769 reaction equation
O[C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][N:8](CC#C)[CH2:9]2)=[CH:4][CH:3]=1.OC1C=C2C(CCN(CC3CC3)C2)=CC=1.C(N(C)C(Cl)=O)C.N1(C(Cl)=O)CCCC1.N1(C(Cl)=O)CCCCC1.N1(C(Cl)=O)CCOCC1>CC#N>[CH2:9]1[C:10]2[C:5](=[CH:4][CH:3]=[CH:2][CH:11]=2)[CH2:6][CH2:7][NH:8]1

Participants

8

Reactant 6

HCID 709371-Pyrrolidinecarbonyl chlorideHCID 848104-Morpholinecarbonyl chlorideHCID 2420851-Piperidinecarbonyl chlorideHCID 11240471N-Ethyl-N-methylcarbamoyl chlorideHCID 67493078HCID 67493078, compoundHCID 866380911018448-54-8

Product 1

HCID 70461,2,3,4-Tetrahydroisoquinoline

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Finally, 7-Hydroxy-N-propargyl-1,2,3,4-tetrahydroisoquinoline (8) and 7-Hydroxy-N-cyclopropylmethyl-1,2,3,4-tetrahydroisoquinoline (9), were added in a solution of N,N-dialkylcarbamyl chloride analogous compound (R2-CO—Cl) (10a-d) in CH3CN, wherein R2 represents, respectively, N-Ethyl-N-methyl amino, 1-Pyrrolidyl, 1-Piperidinyl or 1-Morpholinyl; said R2 possesses a structure of formula (IV), (V), (VI) or (VII), respectively; as such, analogous compound (R2-CO—Cl) (10a-d) were N-ethyl-N-methyl-carbamoyl chloride (10a), pyrrolidine carbonyl chloride (10b), piperidinyl carbonyl chloride (10c) and morpholine carbonyl chloride (10d), respectively, and after step (f), obtained 1,2,3,4-tetrahydroisoquinoline derivatives 11a-d and 12a-d respectively. Above-mentioned N-ethyl-N-methyl-carbamoyl chloride (10a), pyrrolidine carbonyl chloride (10b), piperidine carbonyl chloride (10c) and morpholine carbonyl chloride (10d), were commercially unavailable, but could be synthesized via conventional method as described in reference (1), using a solution of phosgene in toluene to give 10a-d.

Sources & evidence

ORD record
ord-709f53d574de41838d8c332304ffe18c
Source dataset
uspto-grants-2012_05
Patent number
US08173648B2

Reaction notes

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