HCID 12230414, compound → HCID 21389862, compound

HRID 1833606Notes

Reaction equation

C(OC1C=C2C(=CC=1)NC1C(C)(CC(O)=O)OCCC2=1)C1C=CC=CC=1.[ClH:27].C([O:35][C:36]1[CH:37]=[C:38]2[C:42](=[CH:43][CH:44]=1)[N:41]([CH2:45][CH3:46])[C:40]1[C:47]([CH2:52][CH2:53][N:54]([CH3:56])[CH3:55])([CH3:51])[O:48][CH2:49][CH2:50][C:39]2=1)C1C=CC=CC=1>>[ClH:27].[CH3:56][N:54]([CH3:55])[CH2:53][CH2:52][C:47]1([CH3:51])[C:40]2[N:41]([CH2:45][CH3:46])[C:42]3[C:38]([C:39]=2[CH2:50][CH2:49][O:48]1)=[CH:37][C:36]([OH:35])=[CH:44][CH:43]=3

Participants

Reactant 2

HCID 12230414HCID 12230414, compound

HCID 21389859HCID 21389859, compound

Product 1

HCID 21389862HCID 21389862, compound

Procedure

By following the procedure of this example but replacing 6-benzyloxy-1-methyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid with an equivalent amount of 6-benzyloxy-1-[2-(dimethylamino)ethyl]-9-ethyl-1-methyl-1,3,4,9-tetrahydropyrano[3,4-b]indole hydrochloride, described in Example 731b, then 1-[2-(dimethylamino)ethyl]-9-ethyl-1-methyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-6-ol hydrochloride, is obtained m.p. 213° - 214° C; the corresponding free base of the latter compound has nmr (CDCl3) δ 1.36 (t, ν= 7 cps, 3H) 1.6 (s,3H), 2.18 (s,6H). Likewise, replacement with 6-benzyloxy-1,9-dimethyl-1-[2-(dimethylamino)ethyl]-1,3,4,9-tetrahydropyrano[3,4-]indole hydrochloride described in Example 731d, gives 1,9-dimethyl-1-[2-(dimethylamino)ethyl]-1,3,4,9-tetrahydropyrano[3,4-b]indol-6-ol hydrochloride, m.p. 242°-244° C., corresponding free base has nmr (CDCl3) δ 1.6 (s,3H), 2.2 (s,6H), 3.7 (s,3H).

Sources & evidence

ORD record: ord-30df7f71c87f4db681176fba6dd82fa1
Source dataset: uspto-grants-1978_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04066779

Reaction notes

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