Phosgene → HCID 67493078, compound
Reaction equation
[CH2:1]([N:3]([CH3:7])[C:4](Cl)=O)[CH3:2].N1(C(Cl)=O)[CH2:12][CH2:11][CH2:10][CH2:9]1.N1(C(Cl)=O)[CH2:21][CH2:20][CH2:19]CC1.N1(C(Cl)=O)CC[O:28][CH2:27][CH2:26]1.C(Cl)(Cl)=O>C1(C)C=CC=CC=1>[OH:28][C:27]1[CH:9]=[C:10]2[C:11]([CH2:2][CH2:1][N:3]([CH2:7][CH:19]3[CH2:20][CH2:21]3)[CH2:4]2)=[CH:12][CH:26]=1Participants
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.
Workup
- customcould be synthesized via conventional method
- customto give 10a-d
Sources & evidence
- ORD record
- ord-81695f3ee2d2499e86724bbe5dc6df86
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08173648B2
Reaction notes
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