1-(Acetamidomethyl)-1-methyl-1,3,4,9-tetrahydropyrano[3,4-b]indole → 1,3,4,9-Tetrahydro-1-methylpyrano[3,4-b]indol-1-methanamine

HRID 647588Notes

Reaction equation

HRID 647588 reaction equation
[CH3:1][C:2]1([CH2:15][NH:16]C(=O)C)[C:7]2[NH:8][C:9]3[C:14]([C:6]=2[CH2:5][CH2:4][O:3]1)=[CH:13][CH:12]=[CH:11][CH:10]=3.C(C1C=CC=C2C=1NC1C(C)(CN)OCCC2=1)C.COC1C=C2C(C3CCOC(C)(CN)C=3N2)=CC=1.C1(COC2C=C3C(=CC=2)NC2C(C)(CN)OCCC3=2)C=CC=CC=1.C(C1(CN)C2NC3C(C=2CCO1)=CC=CC=3)CC.FC(F)(F)C1C=CC=C2C=1C1CCOC(C(N)C)(C)C=1N2>>[CH3:1][C:2]1([CH2:15][NH2:16])[C:7]2[NH:8][C:9]3[C:14]([C:6]=2[CH2:5][CH2:4][O:3]1)=[CH:13][CH:12]=[CH:11][CH:10]=3

Participants

7

Reactant 6

HCID 127081801-(Acetamidomethyl)-1-methyl-1,3,4,9-tetrahydropyrano[3,4-b]indoleHCID 204850757-Methoxy-1,3,4,9-tetrahydro-1-methylpyrano[3,4-b]indole-1-methanamineHCID 204850768-Ethyl-1,3,4,9-tetrahydro-1-methylpyrano[3,4-b]indole-1-methanamineHCID 204850971-Propyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-methanamineHCID 204850981-(5-Trifluoromethyl-1,3,4,9-tetrahydro-1-methylpyrano[3,4-b]indol-1-yl)-ethanamineHCID 204851256-Phenylmethoxy-1,3,4,9-tetrahydro-1-methylpyrano[3,4-b]indole-1-methanamine

Product 1

HCID 127081811,3,4,9-Tetrahydro-1-methylpyrano[3,4-b]indol-1-methanamine

Procedure

In the same manner but replacing N-[(1,3,4,9-tetrahydro-1-methylpyrano[3,4-b]indol-1-yl)methyl]-acetamide with an equivalent amount of another compound of formula IIa described in Examples 1 and 2, the following compounds of formula V are obtained: respectively: 8-ethyl-1,3,4,9-tetrahydro-1-methylpyrano[3,4-b]indole-1-methanamine, 7-methoxy-1,3,4,9-tetrahydro-1-methylpyrano[3,4-b]indole-1-methanamine, 6-phenylmethoxy-1,3,4,9-tetrahydro-1-methylpyrano[3,4-b]indole-1-methanamine, 1-propyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-methanamine, 1-(1-ethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)propanamine,α-(1-ethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)-benzenemethanamine, α-(1-butyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-yl)-benzeneethanamine,1-(6-chloro-1,3,4,9-tetrahydro-1-methylpyrano[3,4-b]indol-1-yl)-ethanamine,1-(6-nitro-1,3,4,9-tetrahydro-1-methylpyrano[3,4-b]indol-1-yl)ethanamine and 1-(5-trifluoromethyl-1,3,4,9-tetrahydro-1-methylpyrano[3,4-b]indol-1-yl)-ethanamine.

Workup

  1. customthe following compounds of formula V are obtained

Sources & evidence

ORD record
ord-bac0cfb4047b4580b2b7215d6a2dd907
Source dataset
uspto-grants-1983_10
Patent number
US04409224

Reaction notes

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